N-bromobutanimide → 2'-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester

HRID 719730Notes

Reaction equation

HRID 719730 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]=[CH:33][C:32]=2[CH3:37])=[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]=[CH:33][C:32]=2[CH2:37][Br:19])=[CH:27][CH:26]=1)=[O:24])[CH3:21]

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 121718932'-Methylbiphenyl-4-carboxylic acid ethyl esterHCID 214642554'-Bromomethyl-biphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 219992402'-Bromomethyl-biphenyl-4-carboxylic acid ethyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2′-Bromomethyl-biphenyl4-carboxylic acid ethyl ester was synthesized as described for 4′-bromomethyl-biphenyl-3-carboxylic acid ethyl ester. 2′-Methyl-biphenyl-4-carboxylic acid ethyl ester (4.4 g, 18.31 mmol, 1 eq.) in carbon tetrachloride was treated with N-bromosuccinimide (3.58 g, 20.14 mmol, 1.1 eq.), and 2,2′-azobisisobutyronitrile (0.15 g, 0.92 mmol, 5 mol %). When complete, the reaction was worked up as described leaving 2′-bromomethyl-biphenyl-4-carboxylic acid ethyl ester (5.77 g, 99% yield) as a yellow oil.

Workup

  1. custom2′-Bromomethyl-biphenyl4-carboxylic acid ethyl ester was synthesized

Sources & evidence

ORD record
ord-41d7aa59ad0945c0afdc1468984c3bc6
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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