Water → Methyl 5-bromo-3-chloro-2-hydroxy-4-methylbenzoate

HRID 629453Notes

Reaction equation

HRID 629453 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Cl:14]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([Cl:14])[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 11425090Methyl 5-bromo-2-hydroxy-4-methylbenzoate

Product 1

HCID 118468346Methyl 5-bromo-3-chloro-2-hydroxy-4-methylbenzoateYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 5-bromo-2-hydroxy-4-methylbenzoate (4.54 g) in DMF (34.0 mL) was added N-chlorosuccinimide (2.47 g), and the mixture was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (5.20 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6db8542cec8449429c6cbe9a5b05bc67
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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