Water → HCID 19922600, compound

HRID 1647941Notes

Reaction equation

HRID 1647941 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16](O)[CH3:17])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15].P(Br)(Br)[Br:20].O>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]([Br:20])[CH3:17])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 19922613HCID 19922613, compound

Product 1

HCID 19922600HCID 19922600, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Forty (40) grams of 1-[3-chloro-4-(2-oxocyclohexane-1-yl methyl)phenyl]ethanol were dissolved in 300 ml of carbon tetrachloride and then incorporated dropwise with 44.7 g of phosphorus tribromide at a temperature of -15° to -10° C., after which the whole was stirred at said temperature for 30 minutes, withdrawn from the ice bath and then further stirred for one hour. After the completion of the reaction, the reaction mixture was water washed, dried and then freed of the solvent at a reduced pressure to obtain a residue. The residue was adhered to a silica gel-packed column and then eluted with isopropyl ether-hexane (1/2), after which the eluate was freed of the solvent thereby to obtain 46.5 g of 1-[3-chloro-4-(2-oxocyclohexane-1-yl methyl)phenyl]ethylbromide.

Workup

  1. customfor 30 minutes
  2. customwithdrawn from the ice bath
  3. customAfter the completion of the reaction
  4. washwashed
  5. customdried
  6. customto obtain a residue
  7. washeluted with isopropyl ether-hexane (1/2)

Sources & evidence

ORD record
ord-c5d6b7d055144f8bac3bc9d6f3390e40
Source dataset
uspto-grants-1995_07
Patent number
US05434292

Reaction notes

Loading…