1-Bromo-2-iodobenzene → HCID 58239414, compound

HRID 1964489Notes

Reaction equation

HRID 1964489 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.C([Mg]Cl)(C)C.[CH3:14][C:15]1[CH:16]=[C:17]([P:22]([C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[CH:25]=2)Cl)[CH:18]=[C:19]([CH3:21])[CH:20]=1>C1COCC1.CC(OC)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[P:22]([C:24]1[CH:25]=[C:26]([CH3:31])[CH:27]=[C:28]([CH3:30])[CH:29]=1)[C:17]1[CH:16]=[C:15]([CH3:14])[CH:20]=[C:19]([CH3:21])[CH:18]=1

Participants

6

Reactant 3

HCID 114151-Bromo-2-iodobenzeneHCID 4187520BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINEHCID 178418918HCID 178418918, compound

Product 1

HCID 58239414HCID 58239414, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 9.67 g (34.2 mmol) of 1-bromo-2-iodobenzene in 30 ml of THF are added dropwise, at −78° C., 17.6 ml (37.6 mmol) of an isopropylmagnesium chloride solution (2 molar in THF). The mixture is stirred at a temperature between −30° C. and −40° C. for a further 1 hour, then cooled again to −78° C., and a suspension of 10.4 g (37.6 mmol) of bis(3,5-dimethylphenyl)chlorophosphine in 10 ml of THF and 10 ml of TBME are added. The cooling is removed and the reaction mixture is stirred at room temperature overnight. The resulting solution is admixed with 50 ml of water and extracted with water/TBME. The organic phases are collected and dried over sodium sulphate, and the solvent is distilled off under reduced pressure on a rotary evaporator. The solid white crude product is purified by chromatography (silica gel 60; eluent=methylene chloride). The desired product is obtained as a white solid in a yield of 56%.

Workup

  1. additionare added
  2. customThe cooling is removed
  3. stirringthe reaction mixture is stirred at room temperature overnight
  4. extractionextracted with water/TBME
  5. customThe organic phases are collected
  6. dry with materialdried over sodium sulphate
  7. distillationthe solvent is distilled off under reduced pressure on a rotary evaporator
  8. customThe solid white crude product is purified by chromatography (silica gel 60; eluent=methylene chloride)

Sources & evidence

ORD record
ord-08f372f74d4a410e8cda77e765f46122
Source dataset
uspto-grants-2013_04
Patent number
US08415488B2

Reaction notes

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