Dichloromethane → Methyl 2-(bromomethyl)-6-chlorobenzoate

HRID 577214Notes

Reaction equation

HRID 577214 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[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:8]1[CH:9]=[CH:10][CH:11]=[C:2]([Cl:1])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22935202Methyl 2-chloro-6-methylbenzoate

Product 1

HCID 22935208Methyl 2-(bromomethyl)-6-chlorobenzoateYield 95.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 2-chloro-6-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, and evaporated, and the residue was dried in vacuo, affording methyl 2-(bromomethyl)-6-chlorobenzoate (4.06 g, 95% yield), which 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. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-dec41500a3e9461d8c2b05b2034aa94c
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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