2-Chloro-5-(methylsulphonyl)benzoic acid → 4-(methylsulfonyl)-Biphenyl-2-carboxylic acid

HRID 2117457Notes

Reaction equation

HRID 2117457 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>[Cu].[OH-].[NH4+]>[CH3:14][S:11]([C:8]1[CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]([C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:3]=2)=[CH:10][CH:9]=1)(=[O:13])=[O:12]

Participants

4

Reactant 1

HCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Product 1

HCID 574452544-(methylsulfonyl)-Biphenyl-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
127.5 °C

Procedure

A mixture of 4.26 mmol 2-chloro-5-methanesulfonyl-benzoic acid, 0.39 mmol Copper powder and 10 ml ammonium hydroxide 25% was heated at 125-130° C. with stirring for 18 hours. Mixture was cooled to room temperature and filtered. The solid was washed with methanol. The filtrate was concentrated in vacuo. The residue was acidified with HCl 1N to pH=2. The obtained solid was washed with water and dried (HV, 50° C., 1 hour) to yield the title compound. MS (m/e): 214.1 (M−H+, 100%)

Workup

  1. temperatureMixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe solid was washed with methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. washThe obtained solid was washed with water
  6. customdried (HV, 50° C., 1 hour)

Sources & evidence

ORD record
ord-e4203dd85535414e9b9a14541b4c1b22
Source dataset
uspto-grants-2008_10
Patent number
US07442710B2

Reaction notes

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