Dimethylformamide → 3-Bromo-4-hydroxybenzamide

HRID 63268Notes

Reaction equation

HRID 63268 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5](O)=[O:6].C[N:13](C=O)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([NH2:13])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 843683-Bromo-4-hydroxybenzoic acid

Product 1

HCID 151699323-Bromo-4-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-bromo-4-hydroxybenzoic acid (0.5 g) and DMF (0.1 ml) in DCM (10 ml) was added dropwise oxalyl chloride (0.6 ml). After stirring for 2 h, ammonia gas was purged through. After completion of reaction by tlc, the solvent was removed under reduced pressure. The residue was dissolved in water and extracted with ethyl acetate. The organics were dried over sodium sulphate and concentrated in vacuo to yield the title compound, 0.18 g

Workup

  1. customammonia gas was purged through
  2. customAfter completion of reaction by tlc
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organics were dried over sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0753a99e195a453d8e41f72e91d9408a
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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