2-Bromo-5-(trifluoromethyl)benzaldehyde → 1-(2-Bromo-5-(trifluoromethyl)phenyl)ethanol

HRID 1473341노트

반응식

HRID 1473341 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][Mg]Cl>C1COCC1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:3]=1[CH:4]([OH:5])[CH3:14]

참가 물질

5

반응물 2

HCID 70180472-Bromo-5-(trifluoromethyl)benzaldehydeHCID 178418332HCID 178418332, 화합물

생성물 1

HCID 574587951-(2-Bromo-5-(trifluoromethyl)phenyl)ethanol수율 98%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

To a solution of 2-bromo-5-(trifluoromethyl)benzaldehyde (10 g, 39.6 mmol) in THF (40 mL), methyl magnesium chloride (3 M in THF) (26.4 mL, 79.3 mmol) was added at −78° C. dropwise. The reaction was warmed to 25° C. and stirred at this temperature for 1 h under a nitrogen atmosphere. Then the reaction mixture was diluted with water (200 mL) extracted with ethyl acetate (2×200 mL). Organic part was dried over sodium sulfate, filtered and concentrated in vacuum to give the crude compound which was further purified by column chromatography using silica gel (100 to 200 mesh) eluting with 0% to 10% ethyl acetate in hexanes to afford 1-(2-bromo-5-(trifluoromethyl)phenyl)ethanol (10.4 g, 98%) as a clear liquid. MS (ESI, Negative ion) m/z (M−1): 267.0. 1H NMR (400 MHz, DMSO) δ 7.87 (s, 1H), 7.80 (d, J=8.2 Hz, 1H), 7.55 (d, J=8.0 Hz, 1H), 5.68 (d, J=4.2 Hz, 1H), 5.03-4.94 (m, 1H), 1.32 (d, J=6.3 Hz, 3H).

후처리

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. dry with materialOrganic part was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customto give the crude compound which
  6. customwas further purified by column chromatography
  7. washeluting with 0% to 10% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-1f6f4121210a4af6b0e608009c920879
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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