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

HRID 1695813Notes

Reaction equation

HRID 1695813 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-meth yl-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-56d81d2f5222448ea1f72cde4ee36331
Source dataset
uspto-grants-2012_04
Patent number
US08163704B2

Reaction notes

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