Dichloromethane → Methyl 5-(bromomethyl)-2-chlorobenzoate

HRID 577010Notes

Reaction equation

HRID 577010 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClCCl>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 57362636Methyl 2-chloro-5-methylbenzoate

Product 1

HCID 57944070Methyl 5-(bromomethyl)-2-chlorobenzoateYield 95.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 2-chloro-5-methylbenzoate (3.0 g, 16.2 mmol), N-bromosuccinimide (3.0 g, 17.0 mmol), and benzoyl peroxide (catalytic) in anhydrous carbon tetrachloride (50 mL) was stirred at reflux overnight. Dichloromethane (50 mL) was added after cooling to room temperature. The mixture was extracted with 1 N NaOH (2×100 mL). The organic layer was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording methyl 5-(bromomethyl)-2-chlorobenzoate (4.06 g, 95% yield). The product was used without further purification.

Workup

  1. temperatureat reflux overnight
  2. extractionThe mixture was extracted with 1 N NaOH (2×100 mL)
  3. customThe organic layer was recovered
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-0f3009b5ed554a9c99b3d3324416679c
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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