Potassium Carbonate → Tert-butyl 2-(2-bromo-4-cyanophenoxy)acetate

HRID 2390143Notes

Reaction equation

HRID 2390143 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=1[O:10][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 753413-Bromo-4-hydroxybenzonitrile2×HCID 79177tert-Butyl bromoacetate

Product 1

HCID 58521856Tert-butyl 2-(2-bromo-4-cyanophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-bromo-4-hydroxybenzonitrile (Intermediate 43; 25.0 g, 126 mmol) in anhydrous acetone (400 ml) was treated with Potassium carbonate (20.8 g, 151 mmol) and dropwise with tert-butyl bromoacetate (24.5 g, 126 mmol). The reaction mixture was heated at 60° C. for 10 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The crude material was purified by column chromatography (silica) eluting with petroleum ether and ethyl acetate (90:10) to afford the title compound as a brown solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude material was purified by column chromatography (silica)
  4. washeluting with petroleum ether and ethyl acetate (90:10)

Sources & evidence

ORD record
ord-6d69759ac3a54c8a9d4f419b9619ebcc
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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