Potassium Bromide → HCID 77174840, compound

HRID 1666300Notes

Reaction equation

HRID 1666300 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9](OS(C)(=O)=O)[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Br-:19].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([Br:19])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 86629543HCID 86629543, compound

Product 1

HCID 77174840HCID 77174840, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-(3,5-dichlorophenyl)-2-mesyloxyacetate (8.2 g) in dimethylformamide (30 ml) was treated with potassium bromide (4.0 g) at 50° C. for 1.5 hours. The reaction mixture was partitioned between water (200 ml) and ethyl acetate (300 ml). The organic phase was separated and washed twice with water (2×200 ml) and finally with saturated brine solution (200 ml). The ethyl acetate solution was dried and concentrated to dryness giving crude methyl 2-(3,5-dichlorophenyl)-2-bromoacetate (8 g). Filtration through a column of silica gel using dichloromethane as eluent gave the pure substance as an oil (7.4 g).

Workup

  1. customThe reaction mixture was partitioned between water (200 ml) and ethyl acetate (300 ml)
  2. customThe organic phase was separated
  3. washwashed twice with water (2×200 ml) and finally with saturated brine solution (200 ml)
  4. dry with materialThe ethyl acetate solution was dried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-602b5c95884249648066255bcff9c84b
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

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