Benzoyl Peroxide → 5'-(1,3-Benzoxazol-2-yl)-2'-(bromomethyl)-1,1'-biphenyl-3-carbonitrile

HRID 7690

Reaction equation

HRID 7690 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([CH3:24])=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[CH:15]=1.C1C(=O)N([Br:32])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([CH2:24][Br:32])=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 219909755'-(1,3-Benzoxazol-2-yl)-2'-methyl-1,1'-biphenyl-3-carbonitrile

Product 1

HCID 219909715'-(1,3-Benzoxazol-2-yl)-2'-(bromomethyl)-1,1'-biphenyl-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5′-(1,3-benzoxazol-2-yl)-2′-methyl-1,1′-biphenyl-3-carbonitrile (229 mg, 0.74 mmol), n-bromosuccinimide (145 mg, 0.81 mmol), and benzoyl peroxide (9 mg, 0.037 mmol) in carbon tetrachloride (15 mL) was refluxed for 5 h. The solvent was evaporated to dryness and the crude was purified by flash chromatography on silica gel eluting with a gradient of EtOAc:hexanes (0 to 30 min: 0 to 20% EtOAc, 30 to 40 min: 50% EtOAc) to afford 5′-(1,3-benzoxazol-2-yl)-2′-(bromomethyl)-1,1′-biphenyl-3-carbonitrile as a colorless solid.

Workup

  1. temperaturewas refluxed for 5 h
  2. customThe solvent was evaporated to dryness
  3. customthe crude was purified by flash chromatography on silica gel eluting with a gradient of EtOAc

Sources & evidence

ORD record
ord-e5f24134709a4e5289eb9e087aef7de8
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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