Potassium Carbonate → 2-(4-Cyano-3-fluoro-phenoxy)-propionic acid tert-butyl ester

HRID 350975Notes

Reaction equation

HRID 350975 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][C:22](=[O:26])[CH:23](Br)[CH3:24])([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O>[C:17]([O:21][C:22](=[O:26])[CH:23]([O:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)[CH3:24])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 545327tert-Butyl 2-bromopropanoateHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 235293652-(4-Cyano-3-fluoro-phenoxy)-propionic acid tert-butyl esterYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-4-hydroxybenzonitrile (1 g, 7.29 mmol) was dissolved in N,N-dimethyl-formamide (20 mL) and stirred with potassium carbonate (1.1 g, 8.0 mmol) at rt for 2 h. (±) 2-Bromopropionic acid tert-butyl ester (1.67 g, 8.0 mmol) was added and the reaction was stirred at rt for 72 hours. The reaction was quenched into dilute aqueous hydrochloric acid and extracted 2× with ethyl acetate. The pooled organics were dried (Na2SO4) and adsorbed onto silica gel, followed by purification by flash column chromatography (20% ethyl acetate/hexane) to afford 1.8 g colorless oil (93% yield).

Workup

  1. additionwas added
  2. customThe reaction was quenched into dilute aqueous hydrochloric acid
  3. extractionextracted 2× with ethyl acetate
  4. dry with materialThe pooled organics were dried (Na2SO4)
  5. customfollowed by purification by flash column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0a81af99856c494cb48fae2602bf81e6
Source dataset
uspto-grants-2007_02
Patent number
US07183293B2

Reaction notes

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