1,4-Dibromobenzene → (4-Bromophenyl)diphenylphosphine

HRID 866431Notes

Reaction equation

HRID 866431 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.Cl[P:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCCCCC.O1CCCC1>[C:22]1([P:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 66180ChlorodiphenylphosphineHCID 178418339Butyllithium

Product 1

HCID 69773(4-Bromophenyl)diphenylphosphine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To 1.0 mole of n-butyllithium in hexane at -78° C under an inert atmosphere is added dropwise and with efficient stirring 236g of p-dibromobenzene in dry tetrahydrofuran (total volume 500 ml). The resulting solution is stirred at -78° C for 1 hour, then treated dropwise at this temperature with 220.5g of chlorodiphenylphosphine. When this addition is complete, the mixture is allowed to warm to room temperature, then solvent is removed under vacuum. The residue is triturated with two 400-ml portions of methanol, then distilled through a Vigreux column. The cut with bp 165°-170° C (0.15 mm) is recrystallized from ethanol to give 100.5g of p-diphenylphosphinobromobenzene, mp 78°-80° C.

Workup

  1. additionWhen this addition
  2. temperatureto warm to room temperature
  3. customsolvent is removed under vacuum
  4. customThe residue is triturated with two 400-ml portions of methanol
  5. distillationdistilled through a Vigreux column
  6. customThe cut with bp 165°-170° C (0.15 mm) is recrystallized from ethanol

Sources & evidence

ORD record
ord-d67e6a2925e549e59c86a0be8444b10a
Source dataset
uspto-grants-1978_07
Patent number
US04098911

Reaction notes

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