Benzoyl Peroxide → 1-Bromo-4-(bromomethyl)-2-fluorobenzene

HRID 1646549Notes

Reaction equation

HRID 1646549 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[Br:8].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Br:8])[CH2:9][Br:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5732804-Bromo-3-fluorotoluene

Product 1

HCID 116661761-Bromo-4-(bromomethyl)-2-fluorobenzeneYield 85%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-Fluoro-4-bromotoluene (ex. Fluorochem) (24.9 g) in tetrachloromethane was reacted with N-bromosuccinimide (23.5 g) in the presence of benzoyl peroxide and light to give 3-fluoro-4-bromobenzyl bromide (30 g). The bromide was treated with sodium and diethyl malonate as in example 6, subsequent acid hydrolysis afforded 3-(3-fluoro-4-bromophenyl) propanoic acid (10 g).

Sources & evidence

ORD record
ord-5d8873a1e481443fbd82749ddd6fa602
Source dataset
uspto-grants-1993_01
Patent number
US05180737

Reaction notes

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