Benzyl Chloride → 4-(Benzyloxy)-1-bromo-2-(trifluoromethoxy)benzene

HRID 1027238노트

반응식

HRID 1027238 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][C:10]([F:13])([F:12])[F:11].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([O:9][C:10]([F:12])([F:11])[F:13])[CH:4]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

5

반응물 3

HCID 7503Benzyl ChlorideHCID 10796Cesium carbonateHCID 177507434-Bromo-3-(trifluoromethoxy)phenol

생성물 1

HCID 672362364-(Benzyloxy)-1-bromo-2-(trifluoromethoxy)benzene수율 98%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 4-bromo-3-(trifluoromethoxy)phenol (2.97 g, 11.6 mmol) in DMF (10 mL) was added Cs2CO3 (5.65 g, 17.3 mmol) and benzyl chloride (1.46 mL, 12.7 mmol) at RT. The reaction mixture was stirred overnight then quenched with water and diluted with EtOAc. The organic phase was washed with water (3×), brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (EtOAc/Heptane) to afford the title compound as a colorless oil (3.92 g, 98% yield). 1H NMR (METHANOL-d4) δ 7.51 (d, J=9.1 Hz, 1H), 7.40-7.45 (m, 4H), 7.34-7.40 (m, 1H), 6.97 (dd, J=2.5, 1.5 Hz, 1H), 6.82 (dd, J=9.1, 3.0 Hz, 1H), 5.06 (s, 2H).

후처리

  1. customthen quenched with water
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with water (3×), brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (EtOAc/Heptane)

출처 및 근거

ORD 기록
ord-a6f5d0dcec7c479093d8bf9600e3f85b
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729263B2

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