N-bromobutanimide → HCID 57229930, compound

HRID 1609178Notes

Reaction equation

HRID 1609178 reaction equation
C(OCC)(=O)C.CCCCCC.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])=[O:27])=[CH:16][CH:15]=1.[Br:35]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:35][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])=[O:27])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 21226206Ethyl acetate hexaneHCID 57081818HCID 57081818, compound

Product 1

HCID 57229930HCID 57229930, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The starting material can be obtained, for example, as follows: 14.2 g of 4-methyl-2'-carboxybiphenyl (EP 253,310) are dissolved in 60 ml of acetonitrile and 10.7 ml of pyridine and 11.4 ml of trimethylsilylethanol are added. The mixture is treated at 0° with 15.1 g of dicyclohexylcarbodiimide and stirred at this temperature for 3 hours. After this, the reaction mixture is evaporated in a high vacuum, the residue is treated with ether, and dicyclohexylurea is filtered off. After flash chromatography (ethyl acetate/hexane 95:5), 4-methyl-2'-(trimethylsilylethoxycarbonyl)biphenyl is obtained as a slightly yellowish oil. (TLC: ethyl acetate/hexane 95:5) Rf : 0.42. 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, 9H), 0.7 ppm (t, 2H), 4.5 ppm (s, 2H), 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-8cca6ecfbd304a9491576abe0fdd27b3
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

Loading…