N-bromobutanimide → Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

HRID 1757276Notes

Reaction equation

HRID 1757276 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1393873(1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

Product 1

HCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateYield 86.9%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (8.1 g) and azo(bisisobutyronitrile) (130 mg) were added to a solution of compound (B) (9.3 g) in carbontetrachloride (300 ml). The mixture was heated under reflux for 4 hours and then cooled to ambient temperature. Insoluble material was removed by filtration and the filtrate concentrated. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:9 v/v) to give methyl 4'-(bromomethyl)biphenyl-2-carboxylate (C) as a solid (10.9 g), m.p. 48°-50° C.; NMR: 3.65(s,3H), 4.55(s,2H), 7.25-7.60 complex (m,7H), 7.85(d,1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customInsoluble material was removed by filtration
  4. concentrationthe filtrate concentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1:9 v/v)

Sources & evidence

ORD record
ord-a170c0eb83a247f3b98d395a27c053e4
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

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