Triphenylphosphine → Bromine triphenylphosphine

HRID 247673Notes

Reaction equation

HRID 247673 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][Br:21]>C(Cl)Cl>[C:14]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[Br:20][Br:21]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 24408Bromine

Product 1

HCID 44191054Bromine triphenylphosphine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.6 g of triphenylphosphine in 30 ml of methylene chloride was treated dropwise at 0° C. with a solution of 0.519 ml of bromine in 20 ml of methylene chloride until a slight yellow colour persisted. The yellow suspension obtained was cautiously concentrated to dryness on a rotary evaporator and the yellowish, crystalline residue was dried in a high vacuum (0.5 Torr) at room temperature for 1 hour. The triphenylphosphine-bromine obtained was suspended in 50 ml of toluene and the suspension was concentrated to dryness on a rotary evaporator. Thereafter, the residue was suspended in 30 ml of toluene, the suspension was treated with a solution of 2.2 g of p-[trans-4-(2,3-epoxypentyl)cyclohexyl]benzonitrile in 10 ml of toluene and the mixture was stirred for 2 hours at 80° C. bath temperature. Low-pressure chromatography (0.5 bar) of the cooled reaction mixture on silica gel with toluene gave 2.83 g (84%) of p-[trans-4-(2,3-dibromopentyl)cyclohexyl]benzonitrile as a yellowish oil (containing 66.6% erythro form and 32.8% threo form); Rf-value (ethyl acetate/petroleum ether vol. 10:90) 0.33. This material was processed without additional purification.

Workup

  1. customThe yellow suspension obtained
  2. concentrationwas cautiously concentrated to dryness on a rotary evaporator
  3. customthe yellowish, crystalline residue was dried in a high vacuum (0.5 Torr) at room temperature for 1 hour

Sources & evidence

ORD record
ord-ab41f33af275478faca19b7258dc203b
Source dataset
uspto-grants-1987_11
Patent number
US04709030

Reaction notes

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