1,2-Bis(dichlorophosphino)benzene → 1,2-Bis(bis(3,5-diisopropylphenyl)phosphino)benzene

HRID 476324Notes

Reaction equation

HRID 476324 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6](Br)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[Mg].[CH:15]([C:18]1[CH:19]=[C:20]([Mg]Br)[CH:21]=[C:22]([CH:24]([CH3:26])[CH3:25])[CH:23]=1)([CH3:17])[CH3:16].Cl[P:30](Cl)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[P:37](Cl)Cl>C1COCC1>[CH:1]([C:4]1[CH:5]=[C:6]([P:30]([C:6]2[CH:5]=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[P:37]([C:6]2[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)[C:20]2[CH:19]=[C:18]([CH:15]([CH3:17])[CH3:16])[CH:23]=[C:22]([CH:24]([CH3:26])[CH3:25])[CH:21]=2)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 33165621,2-Bis(dichlorophosphino)benzeneHCID 5462224MagnesiumHCID 116300913,5-DiisopropylbromobenzeneHCID 178439359HCID 178439359, compound

Product 1

HCID 866548121,2-Bis(bis(3,5-diisopropylphenyl)phosphino)benzeneYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,5-Diisopropylbromobenzene (3.04 g, 12.60 mmol) was added dropwise to magnesium (0.48 g, 19.75 mmol) and THF (7 mL) in an argon atmosphere. After the dropwise addition, the mixture was heated under reflux for 1 hour. The reaction mixture was cooled to ambient temperature and filtered, and the thus-obtained THF solution of 3,5-diisopropylphenylmagnesium bromide, and 1,2-bis(dichlorophosphino)benzene (0.45 g, 1.61 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 yellow oily substance (1.18 g, yield 74%).

Workup

  1. additionAfter the dropwise addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. filtrationfiltered
  5. customAfter purification

Sources & evidence

ORD record
ord-1e1949f1d47f4a6da13f1bcaf480c786
Source dataset
uspto-grants-2014_01
Patent number
US08637710B2

Reaction notes

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