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

HRID 80296

反応式

HRID 80296 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1382177e666f448d95bd812563dae58c
出典データセット
uspto-grants-2014_09
特許番号
US08846021B2

関連ノート

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