Carbon tetrabromide → HCID 59408358, compound

HRID 2389213Notes

Reaction equation

HRID 2389213 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([C:28]1[CH:33]=[CH:32][C:31]([CH:34]2[CH2:39][CH2:38][CH:37]([CH:40]3[CH2:45][CH2:44][CH:43]([CH:46]=O)[CH2:42][CH2:41]3)[CH2:36][CH2:35]2)=[CH:30][CH:29]=1)[CH2:26][CH3:27]>ClCCl>[Br:2][C:1]([Br:5])=[CH:46][CH:43]1[CH2:42][CH2:41][CH:40]([CH:37]2[CH2:38][CH2:39][CH:34]([C:31]3[CH:30]=[CH:29][C:28]([CH2:25][CH2:26][CH3:27])=[CH:33][CH:32]=3)[CH2:35][CH2:36]2)[CH2:45][CH2:44]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59408347HCID 59408347, compound

Product 1

HCID 59408358HCID 59408358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

34.0 g (0.10 mol) of carbon tetrabromide are initially introduced in 120 ml of dichloromethane, and 53.7 g (0.21 mol) of triphenylphosphine are added in portions. When the addition is complete, the mixture is stirred for 30 min, and a suspension of 16.0 g (51.2 mmol) of 4′-(4-propylphenyl)bicyclohexyl-4-carbaldehyde in 45 ml of dichloromethane is slowly added. The mixture is stirred for 22 h, and the precipitate is filtered off. The filtrate is concentrated to completion, and the residue is purified by column chromatography (SiO2, n-heptane). 4-(2,2-Dibromovinyl)-4′-(4-propylphenyl)bicyclohexyl is obtained as a colourless solid.

Workup

  1. additionWhen the addition
  2. additionis slowly added
  3. stirringThe mixture is stirred for 22 h
  4. filtrationthe precipitate is filtered off
  5. concentrationThe filtrate is concentrated to completion
  6. customthe residue is purified by column chromatography (SiO2, n-heptane)

Sources & evidence

ORD record
ord-51013db62fd64012b15fbd71ad96a301
Source dataset
uspto-grants-2012_09
Patent number
US08273264B2

Reaction notes

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