N-bromobutanimide → Ethyl 2-bromomethyl-3,4-dichlorobenzoate

HRID 1492391Notes

Reaction equation

HRID 1492391 reaction equation
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:14][C:3]1[C:2]([Cl:1])=[C:12]([Cl:13])[CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18950271HCID 18950271, compound

Product 1

HCID 18950258Ethyl 2-bromomethyl-3,4-dichlorobenzoateYield 112.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl 3,4-dichloro-2-methylbenzoate (34.0 g), N-bromosuccinimide (30.0 g) and carbon tetrachloride was irradiated with u.v. light in a photochemical reactor for 3 hours. The cooled mixture was filtered and the filtrate washed with water, dried (magnesium sulphate) and evaporated to give ethyl 2-bromomethyl-3,4-dichlorobenzoate (51.0 g) as an oil, NMR (CDCl3) 1.45 (t,3H), 4.4 (q,2H), 5.15 (s,2H), 7.7 (m,2H).

Workup

  1. customwas irradiated with u.v
  2. filtrationThe cooled mixture was filtered
  3. washthe filtrate washed with water
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated

Sources & evidence

ORD record
ord-22b70368b67a437b86e0a225731c07ce
Source dataset
uspto-grants-1994_12
Patent number
US05374606

Reaction notes

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