Carbon tetrabromide → HCID 21445709, compound

HRID 597591Notes

Reaction equation

HRID 597591 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]([O:32][C:33]1[C:40]([O:41][CH3:42])=[CH:39][C:36]([CH:37]=O)=[CH:35][C:34]=1[O:43][CH3:44])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:37][C:36]1[CH:39]=[C:40]([O:41][CH3:42])[C:33]([O:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:34]([O:43][CH3:44])[CH:35]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 3014502Benzaldehyde, 3,5-dimethoxy-4-(phenylmethoxy)-

Product 1

HCID 21445709HCID 21445709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

The starting material is prepared as follows: To the mixture of 31.5 g of carbon tetrabromide and 65 ml of methylene chloride the solution of 50.0 g of triphenylphosphine in 175 ml of methylene chloride is added dropwise while stirring at 0°-5° under nitrogen. After 20 minutes the solution of 13.5 g of 4-benzyloxy-3,5-dimethoxybenzaldehyde in 50 ml of methylene chloride is added dropwise and the mixture stirred at room temperature for 2 hours. It is washed with 200 ml of water, dried and evaporated. The residue is extracted with hexane-diethyl ether (5:1), the extract evaporated, the residue chromatographed on silica gel, eluted with diethyl ether, the eluate evaporated and the residue recrystallized from hexane, to yield the β,β-dibromo-4-benzyloxy-3,5-dimethoxy-styrene melting at 76°-77°.

Workup

  1. customThe starting material is prepared
  2. additionis added dropwise
  3. stirringthe mixture stirred at room temperature for 2 hours
  4. washIt is washed with 200 ml of water
  5. customdried
  6. customevaporated
  7. extractionThe residue is extracted with hexane-diethyl ether (5:1)
  8. customthe extract evaporated
  9. customthe residue chromatographed on silica gel
  10. washeluted with diethyl ether
  11. customthe eluate evaporated
  12. customthe residue recrystallized from hexane

Sources & evidence

ORD record
ord-2b6bd1ad901641ff99ee4a5dd4f60eee
Source dataset
uspto-grants-1977_03
Patent number
US04014899

Reaction notes

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