Benzene, 1-bromo-3,5-dimethyl- → 1,2-Bis(bis(3,5-dimethylphenyl)phosphino)benzene

HRID 476323

Reaction equation

HRID 476323 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Mg].[CH3:11][C:12]1[CH:13]=[C:14]([Mg]Br)[CH:15]=[C:16]([CH3:18])[CH:17]=1.Cl[P:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[P:29](Cl)Cl>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([P:22]([C:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[P:29]([C:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=2)[C:14]2[CH:13]=[C:12]([CH3:11])[CH:17]=[C:16]([CH3:18])[CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 33165621,2-Bis(dichlorophosphino)benzeneHCID 5462224MagnesiumHCID 178425074HCID 178425074, compound

Product 1

HCID 183243201,2-Bis(bis(3,5-dimethylphenyl)phosphino)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,5-Dimethylbromobenzene (5.54 g, 29.93 mmol) was added dropwise to magnesium (1.07 g, 44.03 mmol) and THF (30 mL) in an argon atmosphere. The reaction mixture was cooled to ambient temperature and filtered, and the thus-obtained THF solution of 3,5-dimethylphenylmagnesium bromide, and 1,2-bis(dichlorophosphino)benzene (0.95 g, 3.39 mmol) were reacted as in Production Example 1. The reaction was allowed to proceed overnight at 60° C. After purification, the title compound was obtained as a white powder (1.45 g, yield 76%).

Workup

  1. filtrationfiltered
  2. customAfter purification

Sources & evidence

ORD record
ord-54025fffc9d94247b3250ce08c963bc2
Source dataset
uspto-grants-2014_01
Patent number
US08637710B2

Linked notes

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