Carbon tetrabromide → 1-(2-Bromoethyl)-3-chlorobenzene

HRID 130690ノート

反応式

HRID 130690 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6]O.C(Br)(Br)(Br)[Br:12]>ClCCl>[Br:12][CH2:6][CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=1

参加物

4

反応物 2

HCID 11205Carbon tetrabromideHCID 78856m-Chlorophenethylic alcohol

生成物 1

HCID 1401401-(2-Bromoethyl)-3-chlorobenzene収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Add triphenylphoshpine (3.90 g, 14.9 mmol) to a stirred solution of 3-chlorophenethyl alcohol (2.0 mL, 14.8 mmol), carbon tetrabromide (4.91 g, 14.8 mmol) and anhydrous dichloromethane (100 mL). Stir for 5 h under nitrogen at room temperature, and then wash with water (100 mL) and brine (100 mL). Dry the dichloromethane layer over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 100% hexanes to yield 2.30 g (71%) of 1-(2-bromo-ethyl)-3-chloro-benzene: TLC: Rf in 100% hexanes: 0.27; 1H NMR (CDCl3): 7.26-7.11 (m, 3H), 7.09-7.07 (m, 1H), 3.54 (t, 2H), 3.12 (t, 2H).

後処理

  1. washwash with water (100 mL) and brine (100 mL)
  2. dry with materialDry the dichloromethane layer over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate on a rotary evaporator
  5. customto give the crude product
  6. customThe crude product is purified by flash chromatography on silica gel eluting with 100% hexanes

出典と根拠

ORDレコード
ord-afcb8c49dbed4a5e98ffd5479e6aeec6
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

反応ノート

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