Hydrochloric Acid → 4-Bromo-2-(trifluoromethoxy)benzoic acid

HRID 1984882노트

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HRID 1984882 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][C:11]([F:14])([F:13])[F:12])[CH:3]=1.S(N)(=O)(=O)[OH:16].O.O.P([O-])(O)(O)=O.[Na+].Cl([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([OH:16])=[O:7])=[C:4]([O:10][C:11]([F:12])([F:13])[F:14])[CH:3]=1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 5987Sulfamic AcidHCID 10340Sodium CarbonateHCID 187000874-Bromo-2-(trifluoromethoxy)benzaldehydeHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, Dihydrate

생성물 1

HCID 166655724-Bromo-2-(trifluoromethoxy)benzoic acid수율 81%

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
4 °C

실험 절차

A solution of 4-bromo-2-trifluoromethoxy-benzaldehyde (550 mg, 2.04 mmol) in 1,4-dioxane (27 mL) and H2O (9 mL) was cooled at 4° C. To the solution were added amidosulfuric acid (296 mg, 3.05 mmol) and sodium dihydrogen phosphate dihydrate (1.4 g, 8.98 mmol). The mixture was stirred at 4° C. for 15 min. To the reaction mixture was added a solution of sodium chlorite (238 mg, 2.63 mmol) in H2O (1.5 mL) and stirred at 4° C. for 15 min. To the reaction mixture was added Na2CO3 (304 mg, 2.41 mmol) and stirred at 4° C. for 15 min. The mixture was acidified with conc-HCl (pH=1), and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography (silica gel, 1% MeOH in CHCl3) to give 4-bromo-2-trifluoromethoxy-benzoic acid (471 mg, 81%) as a white solid.

후처리

  1. stirringstirred at 4° C. for 15 min
  2. stirringstirred at 4° C. for 15 min
  3. extractionthe aqueous layer was extracted with CHCl3 (three times)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography (silica gel, 1% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-229d4df18a5f4f82bc7e229e9dc16474
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544690B2

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