tert-Butyl methyl ether → 5-Phenyl-2-methylbenzylbromide

HRID 2296974Notes

Reaction equation

HRID 2296974 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH3:15])=[C:11]([CH:14]=2)[CH2:12]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:17].COC(C)(C)C>C(OCC)C>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH3:15])=[C:11]([CH:14]=2)[CH2:12][Br:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 24614Phosphorus tribromideHCID 12056528(4-Methylbiphenyl-3-yl)methanol

Product 1

HCID 120565275-Phenyl-2-methylbenzylbromideYield 180.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.33 g (6.71 mmol) of 5-phenyl-2-methylbenzylalcohol in 30 ml of dry diethyl ether was added dropwise 0.91 g (3.02 mmol) of phosphorous tribromide with ice-cooling. After the mixture was stirred for 3 hours with ice-cooling, to the reaction solution were added ice water and tert-butyl methyl ether with ice-cooling. The mixture was stirred for 30 minutes and separated. The organic layer was washed successively with an about 5% aqueous solution of sodium hydrogencarbonate and water, then dried and concentrated to obtain 1.42 g (5.44 mmol) of 5-phenyl-2-methylbenzylbromide as an oil.

Workup

  1. temperaturecooling
  2. temperaturecooling, to the reaction solution
  3. temperaturecooling
  4. stirringThe mixture was stirred for 30 minutes
  5. customseparated
  6. washThe organic layer was washed successively with an about 5% aqueous solution of sodium hydrogencarbonate and water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1fd381171de74c09be973b8ba9a8f774
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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