Methyl 2-bromobenzoate → Methyl 2-[(4-bromophenyl)sulfonyl]benzoate

HRID 2376994

Reaction equation

HRID 2376994 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].O.O.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[Na+]>[Cu]I.CS(C)=O>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 11894Methyl 2-bromobenzoateHCID 23683129Sodium 4-bromobenzene-1-sulfinate--water (1/1/2)

Product 1

HCID 21099525Methyl 2-[(4-bromophenyl)sulfonyl]benzoate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl 2-[(4-bromophenyl)sulfonyl]benzoate was prepared according to the method of Example 135, Step 2 using methyl 2-bromobenzoate (2.8 mL, 20 mmol) in place of (S)-1-(2-iodophenyl)ethanol and sodium 4-bromophenylsulfinate dihydrate (5.6 g, 20 mmol) in place of Intermediate 1, together with CuI (19 g, 100 mmol) and DMSO (40 mL), affording product as a white solid (3.8 g).

Sources & evidence

ORD record
ord-b78c719f709948d286aa5bc8f3621bc0
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Linked notes

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