Diethyl Ether → 3-Bromo-1,1-bis(4-fluorophenyl)propane

HRID 2073481Notes

Reaction equation

HRID 2073481 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10]O)=[CH:4][CH:3]=1.P(Br)(Br)[Br:20].CCOCC>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10][Br:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 197832883,3-Bis(4-fluorophenyl)propanol

Product 1

HCID 138832773-Bromo-1,1-bis(4-fluorophenyl)propane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

50.1 g (0.202 mol) of 3,3-bis(4-fluorophenyl)propanol were dissolved in 150 ml of toluene, and a solution of 21.8 g (0.081 mol) of PBr3 in 50 ml of toluene was added dropwise. The mixture was stirred at room temperature for 30 minutes and at 60° C. for 90 minutes and, for hydrolysis, was poured onto 400 ml of ice, 200 ml of ether were added, the organic phase was separated off, washed with NaHCO3 solution and NaCl solution, dried and concentrated and the residue was distilled in vacuo for purification.

Workup

  1. additionwere added
  2. customthe organic phase was separated off
  3. washwashed with NaHCO3 solution and NaCl solution
  4. customdried
  5. concentrationconcentrated
  6. distillationthe residue was distilled in vacuo for purification

Sources & evidence

ORD record
ord-e191d02e21a043de9c13d75fe7081c88
Source dataset
uspto-grants-1990_04
Patent number
US04918073

Reaction notes

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