Toluene → 4-(Methanesulfonyl)benzoyl chloride

HRID 1402752Notes

Reaction equation

HRID 1402752 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].O=S(Cl)[Cl:16].C1(C)C=CC=CC=1>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:16])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl Chloride2×HCID 77670p-(Methylsulphonyl)benzoic acid

Product 1

HCID 112760134-(Methanesulfonyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-methylsulphonylbenzoic acid (100 mg, 0.48 mmol) in DCM (2 mL) was added SOCl2 (52 μL, 0.73 mmol) and toluene (2 mL) and the resulting reaction was stirred at 60° C. for 20 hours. A further charge of SOCl2 (100 μL, 1.45 mmol) was added and the reaction was heated at 80° C. for a further 24 hours. Volatiles were removed at reduced pressure and the crude product used in subsequent steps without further purification.

Workup

  1. customthe resulting reaction
  2. additionwas added
  3. temperaturethe reaction was heated at 80° C. for a further 24 hours
  4. customVolatiles were removed at reduced pressure
  5. customthe crude product used in subsequent steps without further purification

Sources & evidence

ORD record
ord-376851d3dd934e0a83b40bcfe2e447ff
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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