1,2-Bis(dichlorophosphino)benzene → 1,2-Bis(bis(3,5-bis(2,6-dimethylphenyl)phenyl)phosphino)benzene

HRID 476326

Reaction equation

HRID 476326 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:15])[CH:5]=[C:4]([C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])[CH:3]=1.[Mg].Cl[P:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[P:33](Cl)Cl>C1COCC1>[CH3:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:8]=1[C:6]1[CH:7]=[C:2]([P:26]([C:2]2[CH:3]=[C:4]([C:16]3[C:17]([CH3:23])=[CH:18][CH:19]=[CH:20][C:21]=3[CH3:22])[CH:5]=[C:6]([C:8]3[C:9]([CH3:15])=[CH:10][CH:11]=[CH:12][C:13]=3[CH3:14])[CH:7]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[P:33]([C:2]2[CH:3]=[C:4]([C:16]3[C:17]([CH3:23])=[CH:18][CH:19]=[CH:20][C:21]=3[CH3:22])[CH:5]=[C:6]([C:8]3[C:9]([CH3:15])=[CH:10][CH:11]=[CH:12][C:13]=3[CH3:14])[CH:7]=2)[C:2]2[CH:3]=[C:4]([C:16]3[C:17]([CH3:23])=[CH:18][CH:19]=[CH:20][C:21]=3[CH3:22])[CH:5]=[C:6]([C:8]3[C:9]([CH3:15])=[CH:10][CH:11]=[CH:12][C:13]=3[CH3:14])[CH:7]=2)[CH:3]=[C:4]([C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])[CH:5]=1

Participants

5

Reactant 3

HCID 33165621,2-Bis(dichlorophosphino)benzeneHCID 5462224MagnesiumHCID 154713392~5~-Bromo-1~2~,1~6~,3~2~,3~6~-tetramethyl-1~1~,2~1~:2~3~,3~1~-terphenyl

Product 1

HCID 866548131,2-Bis(bis(3,5-bis(2,6-dimethylphenyl)phenyl)phosphino)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Bromo-3,5-bis(2,6-dimethylphenyl)benzene (2.74 g, 7.50 mmol) was added dropwise to magnesium (0.28 g, 11.52 mmol) and THF (10 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 1-(3,5-bis(2,6-dimethylphenyl))magnesium bromide, and 1,2-bis(dichlorophosphino)benzene (0.28 g, 1.00 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 powder (0.70 g, yield 62%).

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-0001196f94c947389f8fd96cac58b106
Source dataset
uspto-grants-2014_01
Patent number
US08637710B2

Linked notes

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