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Lithium borohydride → (4-Bromo-3-(trifluoromethoxy)phenyl)methanol

HRID 1749454
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HRID 1749454 반응식
[BH4-].[Li+].[Br:3][C:4]1[CH:13]=[CH:12][C:7]([C:8](OC)=[O:9])=[CH:6][C:5]=1[O:14][C:15]([F:18])([F:17])[F:16]>C1COCC1>[Br:3][C:4]1[CH:13]=[CH:12][C:7]([CH2:8][OH:9])=[CH:6][C:5]=1[O:14][C:15]([F:16])([F:18])[F:17]
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참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 59300634Methyl 4-bromo-3-(trifluoromethoxy)benzoate

생성물 1

HCID 54472733(4-Bromo-3-(trifluoromethoxy)phenyl)methanol수율 95.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

To a solution of lithium borohydride (1.16 g, 53.4 mmol) in THF (100 mL) was added methyl 4-bromo-3-(trifluoromethoxy)benzoate (10.6 g, 35.6 mmol) at 0° C., and the resulting solution was heated at 70° C. for 3 h under nitrogen atmosphere. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under vacuum to afford the crude title product (9.17 g, 34 mmol). MS (ESI) m/z 270.1 M+, 272.1 [M+2]+.

후처리

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under vacuum

출처 및 근거

ORD 기록
ord-4038d9651be042f798ac1dea23501f5b
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156798B2

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