4-Hydroxybenzaldehyde → Propanoic acid, 2-bromo-2-methyl-, 4-formylphenyl ester

HRID 80296

반응식

HRID 80296 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:17][C:18]([CH3:23])([CH3:22])[C:19](Br)=[O:20].C(=O)C1C=CC=CC=1>C1COCC1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:19](=[O:20])[C:18]([Br:17])([CH3:23])[CH3:22])=[CH:3][CH:4]=1)=[O:7]

참가 물질

6

반응물 4

HCID 1264-HydroxybenzaldehydeHCID 240BenzaldehydeHCID 8471TriethylamineHCID 886852-Bromo-2-methylpropionyl bromide

생성물 1

HCID 11288716Propanoic acid, 2-bromo-2-methyl-, 4-formylphenyl ester수율 48%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4-hydroxy benzaldehyde (6.1 g, 0.050 mol) and triethylamine (6.1 g, 0.060 mol) was stirred in THF (200 mL) in a round-bottom flask. Bromoisobutyryl bromide (13.6 g, 0.060 mol) was added slowly to the stirring benzaldehyde solution, and the reaction mixture was stirred at room temperature for five hours. The white precipitate that appeared was removed by filtration, and the solvent was removed by rotary evaporation. Purification by column chromatography (eluting with 12% EtOAc in hexane) provided the desired aldehyde (6.5 g) as a white solid. 1H NMR (CDCl3) δ=2.09 (s, 6H), 7.33 (d, J=7.2 Hz, 2H), 7.96 (d, J=7.99 Hz, 2H), 10.02 (s, 1H) ppm; 13C NMR (CDCl3) δ (ppm) 30.4, 55.3, 121.5, 131.3, 134.2, 155.3, 169.6, 175.7, 190.9 ppm.

후처리

  1. customThe white precipitate that appeared was removed by filtration
  2. customthe solvent was removed by rotary evaporation
  3. customPurification
  4. washby column chromatography (eluting with 12% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-1382177e666f448d95bd812563dae58c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846021B2

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