N-bromobutanimide → 3'-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester

HRID 719709

Reaction equation

HRID 719709 reaction equation
C(OC(C1C=C(C2C=CC(C[Br:19])=CC=2)C=CC=1)=O)C.[CH2:20]([O:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=2)=[CH:27][CH:26]=1)=[O:24])[CH3:21].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH2:20]([O:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][Br:19])[CH:32]=2)=[CH:27][CH:26]=1)=[O:24])[CH3:21]

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 208200733'-Methyl-biphenyl-4-carboxylic acid ethyl esterHCID 214642554'-Bromomethyl-biphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 586105873'-Bromomethyl-biphenyl-4-carboxylic acid ethyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

3′-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester was synthesized as described for 4′-bromomethyl-biphenyl-3-carboxylic acid ethyl ester. 3′-Methyl-biphenyl-4-carboxylic acid ethyl ester (3.80 g, 15.81 mmol, 1 eq.) in carbon tetrachloride was treated with N-bromosuccinimide (3.1 g, 17.39 mmol, 1.1 eq.) and 2,2′-azobisisobutyronitrile (0.13 g, 0.79 mmol, 5 mol %). When complete, the reaction was worked up as described leaving 3′-bromomethyl-biphenyl-4-carboxylic acid ethyl ester (4.83 g, 96%) as a yellow oil that crystallized on standing.

Workup

  1. custom3′-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester was synthesized

Sources & evidence

ORD record
ord-da6ecfbec1784bb9aef0c6d42db56224
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Linked notes

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