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

HRID 1883619Notes

Reaction equation

HRID 1883619 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH2:4]O.P(Br)(Br)[Br:17].COC(C)(C)C>C(OCC)C>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH2:4][Br:17]

Participants

5

Reactant 3

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

Product 1

HCID 120565275-Phenyl-2-methylbenzylbromideYield 245.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

14.9 g (75.0 mmol) of 2-methyl-5-phenylbenzyl alcohol was dissolved in 100 ml of anhydrous diethyl ether, and to the resulted solution was dropped 8.12 g (30.0 mmol) of phosphorus tribromide under ice cooling. The mixture was stirred further for 3 hours under ice cooling, then, to the reaction solution was added ice water and t-butyl methyl ether, the mixture was stirred for 30 minutes, then, separated. The organic layer was washed with an about 5 wt % sodium bicarbonate solution and water sequentially, dried over anhydrous magnesium sulfate, then, concentrated to obtain 19.2 g (73.7 mmol) of 2-methyl-5-phenylbenzyl bromide.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customseparated
  3. washThe organic layer was washed with an about 5 wt % sodium bicarbonate solution and water sequentially
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dee1669727d04d7a821c4c9c802bd252
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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