Sodium hydride → 2-Bromo-4-chloro-1-(2,2,2-trifluoroethoxy)-benzene

HRID 992479노트

반응식

HRID 992479 반응식
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[OH:11].[Na].[F:13][C:14]([F:22])([F:21])[CH2:15]CS([O-])(=O)=O>CN(C=O)C>[Br:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:15][C:14]([F:22])([F:21])[F:13]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 696702-Bromo-4-chlorophenol2회HCID 5360545SodiumHCID 214700162,2,2-Trifluoroethyl-methanesulfonate

생성물 1

HCID 225714842-Bromo-4-chloro-1-(2,2,2-trifluoroethoxy)-benzene

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a stirred cold (0° C.) suspension of oil free NaH (0.12 mol, 4.8 g of 60% NaH in mineral oil) in anhydrous DMF (50 mL), a solution of 2-bromo-4-chlorophenol in DMF (50 mL) was added over 30 minutes under nitrogen. The resultant gray suspension of the sodium salt of 2-bromo-4-chlorophenol was treated with neat 2,2,2-trifluoroethylmethane sulfonate (21.4 g, 0.12 mol). The stirred mixture was heated at reflux temperature for 2-3 days. The mixture was cooled in an ice water bath and extracted with diethyl ether (2×100 mL). The combined ether extract was washed with 1N NaOH (3×100 mL), 1N HCl, brine, dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo to provide a golden-yellow oil (18.4 g) which was then distilled in vacuo to afford the title compound as a colorless oil (14.7 g): bp 100-103° C. @ 0.5 torr.

후처리

  1. temperatureThe stirred mixture was heated
  2. temperatureat reflux temperature for 2-3 days
  3. temperatureThe mixture was cooled in an ice water bath
  4. extractionextracted with diethyl ether (2×100 mL)
  5. extractionThe combined ether extract
  6. washwas washed with 1N NaOH (3×100 mL), 1N HCl, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-f36ed8275b294710889e54f9ea7c2f30
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469042B1

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