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

HRID 80296

Reaction equation

HRID 80296 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-1382177e666f448d95bd812563dae58c
Source dataset
uspto-grants-2014_09
Patent number
US08846021B2

Linked notes

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