Carbon Tetrachloride → Methyl 4-bromomethyl-2,3-dichlorobenzoate

HRID 37001Notes

Reaction equation

HRID 37001 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[C:10]([CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:14]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCCCC>[Br:14][CH2:13][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([Cl:1])[C:11]=1[Cl:12]

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 10220067Methyl 2,3-dichloro-4-methylbenzoate

Product 1

HCID 19936848Methyl 4-bromomethyl-2,3-dichlorobenzoateYield 99%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 8003PentaneSolvent

Procedure

A mixture of 40 g (0.183 mol) of methyl 2,3-dichloro-4-methylbenzoate, 34.17 g (0.192 mol) of N-bromosuccinimide, 0.4 g (0.0017 mol) of benzoylperoxide, and 640 mL of carbon tetrachloride was stirred at room temperature while being irradiated with a 150 watt flood lamp for 2.5 hours. Concentration of the filtered reaction mixture under vacuum gave 54 g of material which on trituration with pentane followed by storage of the slurry at 5° C. for 18 hours gave 34.6 g (63.5%) of product; mp 57°-61° C.

Workup

  1. customwhile being irradiated with a 150 watt flood lamp for 2.5 hours
  2. customConcentration of the filtered reaction mixture under vacuum

Sources & evidence

ORD record
ord-dc1aa10ccf634d48a4ebba5f643a9452
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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