Methyl 4-methylbenzoate → Methyl 4-(bromomethyl)benzoate

HRID 2249404Notes

Reaction equation

HRID 2249404 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=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>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][Br:19])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 7455Methyl 4-methylbenzoateHCID 67184N-bromobutanimide

Product 1

HCID 256687Methyl 4-(bromomethyl)benzoateYield 91.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of methyl-p-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 4-methoxy carbonyl benzyl bromide (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-2b1e8847149f4e65ae4c4a7e0951817b
Source dataset
uspto-grants-2008_01
Patent number
US07314878B2

Reaction notes

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