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

HRID 1027238ノート

反応式

HRID 1027238 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a6f5d0dcec7c479093d8bf9600e3f85b
出典データセット
uspto-grants-2014_05
特許番号
US08729263B2

反応ノート

読み込み中…