Carbon tetrabromide → HCID 86658324, compound

HRID 1890274Notes

Reaction equation

HRID 1890274 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[C:6]1([C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:13][NH:14][C:15](=[O:21])[CH:16]([CH3:20])[CH2:17]CO)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:5][CH2:1][CH2:17][CH:16]([CH3:20])[C:15]([NH:14][N:13]=[C:12]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:21]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86658325HCID 86658325, compound

Product 1

HCID 86658324HCID 86658324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 8.1 g (24.3 mmol) of carbon tetrabromide are added to a solution of 6.0 g (20.2 mmol) of N′-(diphenylmethylene)-4-hydroxy-2-methylbutane hydrazide and 6.3 g (24.3 mmol) of triphenylphosphane in 150 ml of dichloromethane. The reaction mixture is stirred at 0° C. for 1 h and then concentrated and purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 2.7 g (37%) of the desired product; (log P(HCOOH): 3.76); 1H-NMR (ppm): δ (DMSO-d6)=1.12 (d, 3H), 1.79-1.86 (m, 1H), 2.33-2.38 (m, 1H), 2.62-2.67 (m, 1H), 4.10-4.14 (m, 1H), 4.25-4.29 (m, 1H), 7.29-7.65 (m, 10H); LC-MS: m/z=359 [M+H]+.

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-292c97eb08f1476fbf48f2e4b3c514da
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

Loading…