tert-Butyl methyl ether → 3-(1-Bromoethyl)biphenyl

HRID 2296981Notes

Reaction equation

HRID 2296981 reaction equation
O[CH:2]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].P(Br)(Br)[Br:17].COC(C)(C)C>C(OCC)C>[Br:17][CH:2]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3]

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 24614Phosphorus tribromideHCID 131027561-(Biphenyl-3-yl)ethanol

Product 1

HCID 183888143-(1-Bromoethyl)biphenylYield 0%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3.97 g (20 mmol) of 3-(1-hydroxyethyl)biphenyl in 60 ml of dry diethyl ether was added dropwise 2.70 g (9.0 mmol) of phosphorous tribromide with ice-cooling, and the mixture was further stirred with ice-cooling for 3 hours. To the reaction solution were added ice water and tert-butyl methyl ether. The mixture was stirred for 30 minutes and separated. The organic layer was washed successively with an about 5% aqueous solution of sodium bicarbonate and water, dried and concentrated to obtain 3.73 g (14.28 nmol) of 3-(1-bromoethyl)biphenyl as an oil.

Workup

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

Sources & evidence

ORD record
ord-515c737405b64e3bb8c99e01d1440d72
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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