Bromine → HCID 68869194, compound

HRID 2105834Notes

Reaction equation

HRID 2105834 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[O:12][CH2:13][CH3:14])[CH3:2].[Br:16]Br>O.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([Br:16])[C:8]([Cl:11])=[CH:7][C:6]=1[O:12][CH2:13][CH3:14])[CH3:2]

Participants

5

Reactant 2

HCID 24408BromineHCID 22494013HCID 22494013, compound

Product 1

HCID 68869194HCID 68869194, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-2-ethoxy-benzoic acid ethyl ester (1.46 g, 6.4 mmol) in 13 mL of water and methylene chloride (1:1 mixture) was added bromine (360 uL, 7 mmol). The reaction was stirred for three days. The organic layer was separated. It was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Purification of the crude residue by flash column chromatography (silica gel, eluting with a gradient of ethyl acetate in hexanes) gave 5-bromo-4-chloro-2-ethoxy-benzoic acid ethyl ester (1.26 g, 64%). LC-MS: 307.1 [(M+H)+].

Workup

  1. customThe organic layer was separated
  2. washIt was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash column chromatography (silica gel
  6. washeluting with a gradient of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-139c3bd04ce845ba82dbecac6fc3a737
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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