Azobisisobutyronitrile → Methyl 3-(bromomethyl)benzoate

Reaction equation

[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([O:9][CH3:10])=[O:8])[CH:2]=1.C1C(=O)N([Br:19])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>>[Br:19][CH2:11][C:1]1[CH:2]=[C:3]([CH:4]=[CH:5][CH:6]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

Reactant 3

HCID 6547Azobisisobutyronitrile

HCID 7435Benzoic acid, 3-methyl-, methyl ester

HCID 67184N-bromobutanimide

Product 1

HCID 517981Methyl 3-(bromomethyl)benzoate

Procedure

Methyl m-toluate was brominated with NBS and AIBN as described in Example 21 to give methyl m-bromomethylbenzoate, and this was further reacted with triethyl phosphite as described in Example 2 without further purification.

Sources & evidence

ORD record: ord-72cd4b260c0043e8aa2503a92dce1f5e
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05242908

Reaction notes

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