Methanol → Methyl 4-Bromo-2-chlorobenzoate

HRID 1635858Notes

Reaction equation

HRID 1635858 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([Cl:15])[CH:7]=1.[CH3:16]O>>[CH3:16][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:6]([Br:5])=[CH:7][C:8]=1[Cl:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 22058730Methyl 4-Bromo-2-chlorobenzoate

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (1.64 ml) was added dropwise to a suspension of 4-bromo-2-chlorobenzoic acid (6.92 g) in methanol, and heated to 60° C. for 2 hours. The solvent was removed in vacuo, the residue redissolved in ethyl acetate, and washed sequentially with 0.5 N sodium hydroxide (2×), water, and brine. The organic phase was dried over anhydrous sodium sulfate, and the solvent removed in vacuo to afford the title compound (7.8 g). 1H NMR (300 MHz), (DMSO-d6) δ: 3.87 (s,3H), 7.68-7.9 (m, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue redissolved in ethyl acetate
  3. washwashed sequentially with 0.5 N sodium hydroxide (2×), water, and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d8fffad2e70348f3b168fac72172cee8
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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