Potassium Carbonate → tert-Butyl 2-(3-bromophenoxy)acetate

HRID 1250110Notes

Reaction equation

HRID 1250110 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[Br:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1>CC(C)=O>[C:6]([O:5][C:3](=[O:4])[CH2:2][O:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([Br:16])[CH:18]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 20577391tert-Butyl 2-(3-bromophenoxy)acetateYield 101.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Tert-butyl bromoacetate (1.88 mL, 12.69 mmol) and potassium carbonate (3.5 g, 25.38 mmol) were added to a solution of 3-bromophenol (2.09 g, 12.08 mmol) in acetone (30 mL), and the mixture was stirred at room temperature for 5 hours under a nitrogen atmosphere. The mixture was filtered, and the filtrate was evaporated to dryness to give (3-bromophenoxy)acetic acid tert-butyl ester as a colorless oil (3.53 g, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-c8c282e68794477584cb4747291fac8a
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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