Bromine → 5-Bromo-2-hydroxy-4-methoxybenzaldehyde

HRID 10634

반응식

HRID 10634 반응식
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:12]Br>ClCCl>[Br:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:2]([OH:1])=[C:3]([CH:6]=1)[CH:4]=[O:5]

참가 물질

4

반응물 2

HCID 24408BromineHCID 696002-Hydroxy-4-Methoxybenzaldehyde

생성물 1

HCID 8181085-Bromo-2-hydroxy-4-methoxybenzaldehyde수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

Ex-29A: 2-Hydroxy-4-methoxybenzaldehyde (6.0 g, 39 mmol) was dissolved in dichloromethane (50 mL) and cooled to 0° C. using an ice-water bath. Bromine (6.8 g, 43 mmol) in dichloromethane (2 mL) was added dropwise to the cooled solution and stirred for 2 h at 0° C. The mixture was warmed to room temperature and stirred for an additional 1 h and the resulting yellow precipitate was collected. Recrystallization (ethyl acetate/hexanes) yielded 7.1 g (80%) of 5-bromo-2-hydroxy-4-methoxybenzaldehyde as white needles, m.p. 63–64° C. 1H-NMR (300 MHz, CDCl3) δ 11.43 (s, 1H), 9.69 (s, 1H), 7.68 (s, 1H), 6.48 (s, 1H), 3.95 (s, 3H). Anal. Calcd. for C8H7BrO3: C, 41.59; H, 3.05. Found: C, 41.86; H, 3.05.

후처리

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for an additional 1 h
  3. customthe resulting yellow precipitate was collected
  4. customRecrystallization (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-361e00b4c4e24068ba682d59610004f6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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