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

HRID 1276109Notes

Reaction equation

HRID 1276109 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>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:12][C:11]1[C:2]([Cl:1])=[C:3]([CH:8]=[CH:9][C:10]=1[S:13]([CH3:16])(=[O:15])=[O:14])[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

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

Product 1

HCID 10969914Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoateYield 70.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

82 g (0.31 mol) of methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate were dissolved in 2 1 of carbon tetrachloride, and 56 g (0.31 mol) of N-bromosuccinimide were added a little at a time while the mixture was exposed to light. The reaction mixture was filtered, the filtrate was concentrated and the residue was taken up in 200 ml of methyl tert-butyl ether. The solution was admixed with petroleum ether and the precipitated solid was filtered off with suction and dried. 74.5 g (70% of theory) of methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate were obtained.

Workup

  1. additionwere added a little at a time while the mixture
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. filtrationthe precipitated solid was filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-ba86fda1a26c4be8bc258dcbc2505e59
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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