Methanol → 168969-13-9

HRID 523638Notes

Reaction equation

HRID 523638 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11]([Cl:14])(=[O:13])=[O:12].O=S(Cl)Cl.[CH3:19]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[CH:4][C:3]=1[S:11]([Cl:14])(=[O:12])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 37373734-Bromo-3-(chlorosulfonyl)benzoic acid

Product 1

HCID 19429197168969-13-9Yield 100%

Conditions

Temperature
80 °C

Procedure

A mixture of 4-bromo-3-chlorosulfonyl-benzoic acid (6.90 g, 23.04 mmol, 1.00 Eq) in SOCl2 (27.41 g, 230.40 mmol, 10.00 Eq) was stirred at 80° C. for 3 hr. Then the solvent was evaporated. The residue was diluted in TOLUENE (50 mL), and MeOH (959.66 mg, 29.95 mmol, 1.30 Eq) was added, the formed mixture was stirred at 110° C. for 2 hr. Solid was formed, and the solvent was evaporated, the solid was washed with PE, and filtered to afford product methyl 4-bromo-3-chlorosulfonyl-benzoate (7.22 g, 23.03 mmol, 99.94% yield) as white solid.

Workup

  1. customThen the solvent was evaporated
  2. additionThe residue was diluted in TOLUENE (50 mL)
  3. stirringthe formed mixture was stirred at 110° C. for 2 hr
  4. customSolid was formed
  5. customthe solvent was evaporated
  6. washthe solid was washed with PE
  7. filtrationfiltered

Sources & evidence

ORD record
ord-11a3d0d46596447398dca54f9bc53acb
Source dataset
uspto-grants-2016_05
Patent number
US09339510B2

Reaction notes

Loading…