Benzoic acid, 3-methyl-, methyl ester → Methyl 3-(bromomethyl)benzoate

HRID 1174501Notes

Reaction equation

HRID 1174501 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1)=[O:4].C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:19][CH2:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

5

Reactant 2

HCID 7435Benzoic acid, 3-methyl-, methyl esterHCID 67184N-bromobutanimide

Product 1

HCID 517981Methyl 3-(bromomethyl)benzoateYield 91.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of methyl-m-toluate (180 g, 1.2 mol) and N-bromosuccimide (235 g, 1.32 mol) in CCl4 (2 L) was added in portion benzoyl peroxide (18 g, 0.1 times) at 50° C. The mixture was refluxed for 5 h. Then the mixture was allowed to cool down to 40° C. and the solid was filtered off. The filtrate was concentrated to give methyl 3-(bromomethyl)benzoate (252 g, 91%) as light yellow liquid.

Workup

  1. temperatureThe mixture was refluxed for 5 h
  2. filtrationthe solid was filtered off
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-181ec4240c1f44e2a3f10bfae9c463b0
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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