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

HRID 1794477노트

반응식

HRID 1794477 반응식
[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

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 10192985HCID 10192985, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-01dbdc62e7224b0d89d4f20162a2637c
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022733B2

반응 노트

불러오는 중…