Boron tribromide → 7-Bromomethyl-5-methoxy-2-(4-methoxy-phenyl)-benzofuran

HRID 1794477ノート

反応式

HRID 1794477 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20]O)[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.B(Br)(Br)[Br:23]>ClCCl>[Br:23][CH2:20][C:5]1[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=[C:3]([O:2][CH3:1])[CH:4]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 10192985HCID 10192985、化合物

生成物 1

HCID 102867967-Bromomethyl-5-methoxy-2-(4-methoxy-phenyl)-benzofuran

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

Benzyl Alcohol 3 (1.02 g, 3.59 mmole) was dissolved in dichloromethane (70 mL) and cooled to −78° C. in an dry ice/acetone bath. Boron tribromide (1.0 M in dichloromethane), (3.95 mL, 3.95 mmole) was added drop wise over 15 minutes. After 30 minutes, the light orange solution was allowed to come to room temperature and reacted for an additional four hours. The solution was concentrated and added to saturated sodium bicarbonate, and extracted with ethyl acetate. Organic layers were combined and washed with water and brine, dried over magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 9:1) to afford 2.91 g (81%) of benzyl bromide17 as a white solid: Mp=158–160° C.; 1H NMR (DMSO-6) δ 7.88(d, 2 H, J=8.8 Hz), 7.23 (s, 1 H), 7.11 (d, 2 H, J=2.5 Hz), 7.09 (d, 2 H, J=8.9 Hz), 6.99 (d, 1 H, J=2.5 Hz), 4.96 (s, 2 H), 3.82 (s, 3 H), 3.80 (s, 3 H).

後処理

  1. customto come to room temperature
  2. customreacted for an additional four hours
  3. concentrationThe solution was concentrated
  4. additionadded to saturated sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe organic phases were concentrated
  9. customchromatographed with silica gel (hexanes:ethyl acetate, 9:1)
  10. customto afford 2.91 g (81%) of benzyl bromide17 as a white solid

出典と根拠

ORDレコード
ord-01dbdc62e7224b0d89d4f20162a2637c
出典データセット
uspto-grants-2006_04
特許番号
US07022733B2

反応ノート

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