Methanol → Methyl 4-Bromo-2-chlorobenzoate

HRID 2410519Notes

Reaction equation

HRID 2410519 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>>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:16])=[O:11])=[C:8]([Cl:15])[CH:7]=1

Participants

4

Reactant 3

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

Product 1

HCID 22058730Methyl 4-Bromo-2-chlorobenzoateYield 82%

Procedure

Thionyl chloride (1.23 mL, 17.0 mmol) was added dropwise into a solution of 4-bromo-2-chlorobenzoic acid (Combi-Blocks CA-4187, 1.0 g, 4.25 mmol) in MeOH (20 mL) at 0° C. The reaction mixture was then stirred at RT until completion. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc and washed with a saturated aqueous solution of NaHCO3 and brine. The organic layer was dried (MgSO4) and concentrated under vacuum to give the title compound (871 mg, 82%). 1H NMR (CDCl3, 300 MHz) δ 7.72 (d, J=8.4 Hz, 1H), 7.64 (d, J=1.9 Hz, 1H), 7.46 (dd, J=8.4, 1.9 Hz, 1H), 3.93 (s, 3H). HPLC (Method A) Rt 4.22 min (Purity: 98.5%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with a saturated aqueous solution of NaHCO3 and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7ff9c0a52c8d45f2a4c6af8c9cae3e76
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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