Carbon tetrabromide → HCID 12018441, compound

HRID 275688Notes

Reaction equation

HRID 275688 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11](Br)(Br)([Br:13])[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:12][C:11]([Br:13])=[CH:4][C:3]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 134042,4-Dichlorobenzaldehyde

Product 1

HCID 12018441HCID 12018441, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of 2,4-dichlorobenzaldehyde (8.7 g, 50 mmol) and carbon tetrabromide (18.3 g, 55 mmol) in dichloromethane (200 ml) was added portionwise triphenylphosphine (28.8 g, 10 mmol) at 0° C. The slightly yellow mixture was stirred at room temperature for 1 hour and diluted with hexanes (800 ml). This mixture was then filtrated through a short silica gel column with 1:10 ethyl acetate-hexanes and the filtrate was concentrated in vacuo to give a white solid (16.5 g, 100%). recrystallization from ether-hexanes gave a white crystalline product (14.2 g, 86% yield); 1H NMR (TMS/CDCl3):

Workup

  1. filtrationThis mixture was then filtrated through a short silica gel column with 1:10 ethyl acetate-hexanes
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ca95d610605f49c784332b1e39b8b2d1
Source dataset
uspto-grants-2002_03
Patent number
US06352990B1

Reaction notes

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