2-Aminophenol → 2-bromo-N-(2-hydroxyphenyl)-2-methylpropionamide

HRID 1258805Notes

Reaction equation

HRID 1258805 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Br:9][C:10]([CH3:15])([CH3:14])[C:11](Br)=[O:12].C(N(CC)CC)C>C(Cl)Cl>[Br:9][C:10]([CH3:15])([CH3:14])[C:11]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])=[O:12]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 8471TriethylamineHCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 146849852-bromo-N-(2-hydroxyphenyl)-2-methylpropionamideYield 921%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-aminophenol (10 g, 9.2 mmol) in DCM (92 mL) at 0° C. was added 2-bromoisobutyryl bromide (11.4 mL, 9.17 mmol) followed by triethyl amine (12.7 mL, 9.2 mmol) and stirred the reaction mixture at 0° C. for 4 h. Reaction mixture was diluted with DCM 100 mL and then washed with water 100 mL dried over sodium sulfate, concentrated on rotavap to give 2-Bromo-N-(2-hydroxy-phenyl)-2-methyl-propionamide (21.8 g) brown solid which was used for next reaction without purification

Workup

  1. customReaction mixture
  2. washwashed with water 100 mL
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated on rotavap

Sources & evidence

ORD record
ord-75fda90d1401437cab8c4836ab3e9fe4
Source dataset
uspto-grants-2013_06
Patent number
US08466114B2

Reaction notes

Loading…