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

HRID 2167420Notes

Reaction equation

HRID 2167420 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>ClC(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-methylsulfonylbenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

82 g (0.1 mol) of methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate are dissolved in 2 l of tetrachloromethane, and 56 g (0.31 mol) of N-bromosuccinimide are added in portions with exposure 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 treated with petroleum ether and the solid which had precipitated was filtered off with suction and dried. This gave 74.5 g (70% of theory) of methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionThe solution was treated with petroleum ether
  4. customthe solid which had precipitated
  5. filtrationwas filtered off with suction
  6. customdried

Sources & evidence

ORD record
ord-2212d74e570641acbd23b9c07df4aa65
Source dataset
uspto-grants-2015_06
Patent number
US09045465B1

Reaction notes

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