Methanol → Methyl 4-bromo-2-ethylbenzoate

HRID 878660Notes

Reaction equation

HRID 878660 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH2:11][CH3:12])[CH:3]=1.O=S(Cl)Cl.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([CH2:11][CH3:12])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 106570054-Bromo-2-ethylbenzoic acid

Product 1

HCID 53797189Methyl 4-bromo-2-ethylbenzoateYield 87%

Conditions

Temperature
70 °C

Procedure

Charged compound 4-bromo-2-ethylbenzoic acid (2.05 g, 9.58 mmol) and methanol (20 mL) to a flask, SOCl2 (3.42 g, 28.74 mmol) was added slowly at 0° C. The reaction mixture was heated to 70° C. for three hour. Solvent was removed and the residue was dissolved in CH2Cl2, filtered, the filtrate was concentrated to a residue which was purified by flash column chromatograph to give 1.9 g of the title compound (87%).

Workup

  1. customSolvent was removed
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to a residue which
  5. customwas purified by flash column chromatograph

Sources & evidence

ORD record
ord-58263e44125e45d6ac238337f47c409e
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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