Allyl bromide → 2-allyloxy-5-bromobenzoic acid

HRID 427744Notes

Reaction equation

HRID 427744 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-:12].[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19]>CN(C=O)C>[CH2:17]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[C:7]([OH:12])=[O:8])[CH:18]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 87071652-allyloxy-5-bromobenzoic acidYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-salicylaldehyde (20.1 g, 100 mM) in DMF (50 ml) was treated with potassium carbonate (20.7 g, 150 mM) and allyl bromide (12.7 g, 10.5 mM). The reaction was stirred at ambient temperature for 18 hours. The reaction was partitioned between ethyl acetate/water. The organic phase was washed with water four times, dried (MgSO4) and evaporated at reduced pressure to give 2-allyloxy-5-bromobenzoic acid as a pale yellow oil (10.0 g, 41 %).

Workup

  1. customThe reaction was partitioned between ethyl acetate/water
  2. washThe organic phase was washed with water four times
  3. dry with materialdried (MgSO4)
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-6a6fe4789a62481b87e7327836099939
Source dataset
uspto-grants-2001_11
Patent number
US06313148B1

Reaction notes

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