Allyl bromide → 3-Methoxy-4-chloro-benzoic acid allyl ester

HRID 450921Notes

Reaction equation

HRID 450921 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=1[O:21][CH3:22]>CN(C)C=O>[CH2:7]([O:18][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:12]([Cl:11])=[C:13]([O:21][CH3:22])[CH:14]=1)[CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 20633784-Chloro-3-methoxybenzoic acid

Product 1

HCID 674384813-Methoxy-4-chloro-benzoic acid allyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (4.44 g, 32.156 mmol) and allyl bromide (2.78 ml, 32.156 mmol) were added to a stirred solution of 4-chloro-3-methoxybenzoic acid (3 g, 16.078 mmol) in N,N-dimethylformamide (30 ml) and allowed to stir at room temperature for 18 hours. The reaction mixture was partitioned between diethyl ether (200 ml) and water (150 ml), the organic phase extracted and further washed with water (150 ml), dried over sodium sulfate and concentrated in vacuo to afford the title compound as an orange oil in 98% yield, 3.57 g.

Workup

  1. customThe reaction mixture was partitioned between diethyl ether (200 ml) and water (150 ml)
  2. extractionthe organic phase extracted
  3. washfurther washed with water (150 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2596488e35054885b587e0b2356950f3
Source dataset
uspto-grants-2013_07
Patent number
US08486992B2

Reaction notes

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