N-bromobutanimide → Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

HRID 2302138Notes

Reaction equation

HRID 2302138 reaction equation
[Cl:1][C:2]1[C:11]([CH3:12])=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:17]N1C(=O)CCC1=O>>[Cl:1][C:2]1[C:11]([CH2:12][Br:17])=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 15132838Methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate

Product 1

HCID 10969914Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

Procedure

80 g (0.3 mol) of methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate, 54 g (0.31 mol) of N-bromosuccinimide and 1.5 g of azoisobutyronitrile are stirred at 76° C. for 6 h. The reaction mixture is filtered and freed form the solvent under reduced pressure. Yield: 104 g; m.p. 83-85° C.

Workup

  1. filtrationThe reaction mixture is filtered

Sources & evidence

ORD record
ord-52162fff8047469d9d63b1f0814f3506
Source dataset
uspto-grants-2002_08
Patent number
US06432881B1

Reaction notes

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