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Isopropyl Acetate → 4-(Bromomethyl)-3-(trifluoromethyl)benzoic acid

HRID 13778
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HRID 13778 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].C(OC(C)C)(=O)C.[Br:22]([O-])(=O)=O.[Na+].S([O-])(O)=O.[Na+]>O>[Br:22][CH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7915Isopropyl AcetateHCID 27755924-Methyl-3-(trifluoromethyl)benzoic acidHCID 23665763Sodium BisulfiteHCID 23668195Sodium Bromate

생성물 1

HCID 231458934-(Bromomethyl)-3-(trifluoromethyl)benzoic acid수율 60.1%

시약·촉매·용매 1

HCID 962Water
용매
2회

실험 절차

To 60.0 g of 4-methyl-3-trifluoromethylbenzoic acid was added 600 ml of isopropyl acetate. Under stirring at room temperature, a solution of 133.0 g of sodium bromate in 420 ml of water and a solution of 91.7 g of sodium hydrogensulfite in 180 ml of water were added in turn. The mixture was gradually heated from 30° C. up to 50° C. at intervals of 10° C. and stirred until the color of the reaction solution disappeared. The aqueous layer was separated to remove, and to the organic layer were added a solution of 133.0 g of sodium bromate in 420 ml of water and a solution of 91.7 g of sodium hydrogensulfite in 180 ml of water, and then the mixture was gradually heated up to 60° C. as above. After separation, to the organic layer were further added a solution of 133.0 g of sodium bromate in 420 ml of water and a solution of 91.7 g of sodium hydrogensulfite in 180 ml of water, and the mixture was gradually heated as above and heated to the temperature the mixture was finally refluxed. After the completion of the reaction, the reaction solution was separated, the organic layer was washed twice with a 5% aqueous sodium thiosulfate solution and twice with 15% saline, dried over anhydrous magnesium sulfate, and, then the solvent was distilled off under reduced pressure. To the residue was added 120 ml of n-heptane, the mixture was stirred, and then the crystals were collected by filtration to obtain 50.0 g of the objective compound as colorless crystals.

후처리

  1. temperatureThe mixture was gradually heated from 30° C. up to 50° C. at intervals of 10° C.
  2. stirringstirred until the color of the reaction solution
  3. customThe aqueous layer was separated
  4. customto remove
  5. additionto the organic layer were added a solution of 133.0 g of sodium bromate in 420 ml of water
  6. temperaturea solution of 91.7 g of sodium hydrogensulfite in 180 ml of water, and then the mixture was gradually heated up to 60° C. as above
  7. customAfter separation
  8. additionto the organic layer were further added a solution of 133.0 g of sodium bromate in 420 ml of water
  9. temperaturea solution of 91.7 g of sodium hydrogensulfite in 180 ml of water, and the mixture was gradually heated as above and
  10. temperatureheated to the temperature the mixture
  11. temperaturewas finally refluxed
  12. customAfter the completion of the reaction
  13. customthe reaction solution was separated
  14. washthe organic layer was washed twice with a 5% aqueous sodium thiosulfate solution and twice with 15% saline
  15. dry with materialdried over anhydrous magnesium sulfate
  16. distillationthe solvent was distilled off under reduced pressure
  17. additionTo the residue was added 120 ml of n-heptane
  18. stirringthe mixture was stirred
  19. filtrationthe crystals were collected by filtration

출처 및 근거

ORD 기록
ord-d4435aab212941fdaa4e2f6e47c96c09
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728131B2

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