Bromomethylcyclopropane → 2-Chloro-5-cyclopropylmethanesulfonyl-benzoic acid

HRID 736135Notes

Reaction equation

HRID 736135 reaction equation
[Cl:1][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].Cl[C:16]1C=CC(S(O)=O)=[CH:21][C:17]=1C(O)=O.BrCC1CC1>C1(CO)CC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][CH:21]2[CH2:17][CH2:16]2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 23291322-Chloro-5-(methylsulphonyl)benzoic acidHCID 151129042-Chloro-5-sulfino-benzoic acid

Product 1

HCID 435605642-Chloro-5-cyclopropylmethanesulfonyl-benzoic acidYield 8%

Reagents, catalysts & solvents 1

HCID 75644CyclopropanemethanolSolvent

Procedure

The title compound was synthesised according to the procedure described for the synthesis of 2-Chloro-5-methanesulfonyl-benzoic acid from 2-Chloro-5-sulfino-benzoic acid and Bromomethyl-cyclopropane (+catalytic amount 12) in 20 ml cyclopropyl methanol/20 ml water and obtained in 8% yield. MS (m/e): 273.1 (MH−, 100%).

Workup

  1. customobtained in 8% yield

Sources & evidence

ORD record
ord-26a2cbcb1e084c1eb64c80c9f4dd3042
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Reaction notes

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