Water → Prop-2-en-1-yl 5-bromo-2-hydroxybenzoate

HRID 1383291Notes

Reaction equation

HRID 1383291 reaction equation
[Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH2:12](Br)[CH:13]=[CH2:14].C(=O)(O)[O-].[Na+].O>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:6]([C:7]([O:9][CH2:14][CH:13]=[CH2:12])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 69725-Bromosalicylic acidHCID 7841Allyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 15541258Prop-2-en-1-yl 5-bromo-2-hydroxybenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromosalicylic acid (10 g, 46 mmol), allyl bromide (6.12 g, 51 mmol) and sodium bicarbonate (4.65 g, 55 mmol) in 50 ml of DMF was stirred under a drying tube for 72 hr. The reaction mixture was poured into water, extracted with ethyl acetate. and the organic layer dried over MgSO4. Concentration under vacuum gave 10.73 g (91%) of product (1-Scheme 2) with the expected NMR.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialand the organic layer dried over MgSO4
  3. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-df1d6b08c38d43e9ae0452dc4e9d91ad
Source dataset
uspto-grants-2001_07
Patent number
US06255298B1

Reaction notes

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