N-bromobutanimide → HCID 57229930, compound

HRID 1739068Notes

Reaction equation

HRID 1739068 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])=[CH:4][CH:3]=1.[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:21])([CH3:20])[CH3:22])=[O:15])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57081818HCID 57081818, compound

Product 1

HCID 57229930HCID 57229930, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

312 mg of 4-methyl-2'-(trimethylsilylethoxycarbonyl)biphenyl, 178 mg of N-bromosuccinimide, 5 mg of azoisobutyronitrile and 15 ml of carbon tetrachloride are heated to reflux for one hour. After cooling, the mixture is evaporated. Flash chromatography (ethyl acetate/hexane 95:5) yields 4-bromomethyl-2'-(trimethylsilylethoxycarbonyl)biphenyl as a slightly yellowish oil. 1H-NMR (CFCl3): 0 ppm (s, 9 H), 0.7 ppm (t, 2 H), 4.5 ppm (s, 2 H), 7.1-8 ppm aromatics.

Workup

  1. temperatureto reflux for one hour
  2. temperatureAfter cooling
  3. customthe mixture is evaporated

Sources & evidence

ORD record
ord-86b5b6668afa4cf38d9bbba466b813eb
Source dataset
uspto-grants-1999_10
Patent number
US05965592

Reaction notes

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