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

HRID 2390111Notes

Reaction equation

HRID 2390111 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>[C:22]([O:21][C:19](=[O:20])[CH2:18][O:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Br:1])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

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

Product 1

HCID 58521856Tert-butyl 2-(2-bromo-4-cyanophenoxy)acetateYield 100.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-bromo-4-hydroxybenzonitrile (Lancaster; 3.00 g; 15.2 mmol) in acetone (30 mL) was treated with potassium carbonate (2.30 g; 16.7 mmol), stirred for 10 minutes then treated with tert-butyl bromoacetate (2.24 mL; 15.2 mmol). The reaction mixture was stirred at 65° C. for 18 hours, then the mixture was filtered, the solid was washed with acetone and the filtrate was concentrated to dryness under vacuum to give the title compound as a yellow sticky solid (4.75 g, quant).

Workup

  1. stirringThe reaction mixture was stirred at 65° C. for 18 hours
  2. filtrationthe mixture was filtered
  3. washthe solid was washed with acetone
  4. concentrationthe filtrate was concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-a23fd59e160e48d9b3f5d15690106a84
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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