3-Bromophenol → tert-Butyl 2-(3-bromophenoxy)acetate

HRID 1817162Notes

Reaction equation

HRID 1817162 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:11]([O:15][C:16](=[O:19])[CH2:17]Br)([CH3:14])([CH3:13])[CH3:12]>CN(C)C=O>[C:11]([O:15][C:16](=[O:19])[CH2:17][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 115633-BromophenolHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 20577391tert-Butyl 2-(3-bromophenoxy)acetateYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

3-Bromophenol (20.4 g, 118 mmol) dissolved in dry N,N-dimethylformamide was carefully treated with sodium hydride (4 g, 167 mmol). t-Butylbromoacetate (23 g, 118 mmol) was added and the mixture heated to 75° C. for 90 minutes. The reaction was concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was washed with saturated ammonium acetate and concentrated in vacuo to yield 28.9 g of tert-butyl(3-bromophenoxy)acetate.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with saturated ammonium acetate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cac6717028294a33be049bcd459654a9
Source dataset
uspto-grants-2009_10
Patent number
US07598251B2

Reaction notes

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