Benzyl Bromide → 3-(Benzyloxy)-2,2-difluoropropan-1-OL

HRID 2279884

반응식

HRID 2279884 반응식
[F:1][C:2]([F:7])([CH2:5][OH:6])[CH2:3][OH:4].FC1C=CC(B(O)O)=CC=1.C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:24]([O:4][CH2:3][C:2]([F:7])([F:1])[CH2:5][OH:6])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 957442,2-Difluoropropane-1,3-diol2회HCID 2856454-Fluorophenylboronic acid

생성물 1

HCID 584638693-(Benzyloxy)-2,2-difluoropropan-1-OL수율 50%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of 2,2-difluoropropane-1,3-diol (Compound 59I, 6.0 g, 53.5 mmol), 4-fluorophenylboronic acid (1.5 g, 10.7 mmol) and K2CO3 (11.0 g, 80.3 mmol) in DMF (50 mL) was treated with benzyl bromide (8.9 mL, 74.9 mmol). The reaction mixture was stirred at RT for 72 h, diluted with ethyl acetate (200 mL) and washed with water (5×100 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give yellow oil which was purified by column chromatography (SiO2, 20% ethyl acetate/hexanes) to give 5 g (50%) of the desired product as an oil. 1H NMR (500 MHz, CDCl3) δ 7.38-7.34 (m, 5H), 4.70 (s, 2H), 3.89-3.88 (m, 2H), 3.77 (t, J=12.6 Hz, 2H).

후처리

  1. washwashed with water (5×100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give yellow oil which
  6. customwas purified by column chromatography (SiO2, 20% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-f744759d3a4745b4a3e913426fd41e1d
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133224B2

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