Dimethyl Sulfate → 1-Chloro-3-fluoro-2-(methoxymethyl)benzene

HRID 266589

반응식

HRID 266589 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][OH:5].[OH-].[Na+].S(OC)(O[CH3:17])(=O)=O>ClCCl.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][O:5][CH3:17]

참가 물질

7

반응물 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 918682-Chloro-6-fluorobenzyl alcohol

생성물 1

HCID 537737161-Chloro-3-fluoro-2-(methoxymethyl)benzene수율 50.2%

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

2-Chloro-6-fluorobenzyl alcohol (50 g) was stirred in dichloromethane and a solution of sodium hydroxide (32 g) in water was added. After 30 minutes stirring the mixture was cooled to 0° C. when dimethyl sulphate (47 g) and tetrabutyl-ammonium hydrogen-sulphate (1 g) were added dropwise. The mixture was allowed to warm to room temperature and stirred for 3 hours. It was quenched with water and extracted with dichloromethane. The organic extract was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue distilled under reduced pressure yielding 1-chloro-3-fluoro-2-methoxymethylbenzene (27.3 g) b.p. 82°-95° C./24 mm Hg.

후처리

  1. additionwere added dropwise
  2. stirringstirred for 3 hours
  3. customIt was quenched with water
  4. extractionextracted with dichloromethane
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried (anhydrous magnesium sulphate)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. distillationthe residue distilled under reduced pressure

출처 및 근거

ORD 기록
ord-e42036ea766a4b53b9c8307ff400b3a9
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650533

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