Carbon tetrabromide → HCID 54450607, compound

HRID 2309765Notes

Reaction equation

HRID 2309765 reaction equation
[C:1]1(/[C:7](/[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:8](/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)\[CH2:9][CH2:10]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:46]>C(#N)C>[Br:46][CH2:10][CH2:9][C:8]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 13298067HCID 13298067, compound

Product 1

HCID 54450607HCID 54450607, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

33.0 g of (Z)-1,2-diphenyl-1-(4-methoxyphenyl)-1-buten-4-ol are dissolved in 500 ml of dry acetonitrile. Then 39.3 g of triphenylphosphine and 49.8 g of carbon tetrabromide are added while stirring. The stirring is continued for 1 h at room temperature. The solvent is evaporated and the evaporation residue is dissolved in hot petrol ether. The insoluble material is removed by filtration. The mother liquor is evaporated, and the evaporation residue is recrystallized from methanol. The yield of the product is 26.7 g (68%) having m.p. 116°-8° C.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe evaporation residue is dissolved in hot petrol ether
  3. customThe insoluble material is removed by filtration
  4. customThe mother liquor is evaporated
  5. customthe evaporation residue is recrystallized from methanol

Sources & evidence

ORD record
ord-ae6c69e11ae4406f930ded520e73d708
Source dataset
uspto-grants-1987_09
Patent number
US04696949

Reaction notes

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