1,3-Dibromobenzene → HCID 11233124, compound

HRID 562874Notes

Reaction equation

HRID 562874 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[Li]CCCC.[C:14]1([P:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[Br:8][C:4]1[CH:3]=[C:2]([P:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 79271,3-DibromobenzeneHCID 66180ChlorodiphenylphosphineHCID 178418339Butyllithium

Product 1

HCID 11233124HCID 11233124, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,3-dibromobenzene (7.4 mL, 61 mmol, 1.05 equiv) in THF (70 mL, 0.9 M) at −90° C. was added n-BuLi (2.5 M) (25.5 mL, 64 mmol, 1.10 equiv) dropwise. The reaction mixture was stirred 45 min then diphenylchlorophosphine (10.7 mL, 58 mmol, 1.0 equiv) was added dropwise and the resulting dark brown solution was warmed to room temperature for 15 min and filtered through a small pad of Celite. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (Et2O/hexane, 0:100-5:95) to afford (3-bromophenyl)diphenylphosphine (2) (18.1 g, 91%) as a viscous colorless oil, which was characterized as follows:

Workup

  1. filtrationfiltered through a small pad of Celite
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography (Et2O/hexane, 0:100-5:95)

Sources & evidence

ORD record
ord-55afa2ec66764d5daf601b33510475e4
Source dataset
uspto-grants-2011_11
Patent number
US08067440B2

Reaction notes

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