Phosphorus tribromide → 4-(4-Methylthiophenoxy)benzylbromide

HRID 1591108Notes

Reaction equation

HRID 1591108 reaction equation
P(Br)(Br)[Br:2].[CH3:5][C:6]1[CH:20]=[CH:19][C:9]([S:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15]O)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1>CCOCC>[CH3:5][C:6]1[CH:20]=[CH:19][C:9]([S:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][Br:2])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 537292604-(4-Methylthiophenoxy)benzyl alcohol

Product 1

HCID 1317178844-(4-Methylthiophenoxy)benzylbromideYield 183.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred mixture of phosphorus tribromide (1.20 g, 4.43 mM) and dry ether (100 ml) was added a solution (20 ml) of 4-(4-methylthiophenoxy)benzyl alcohol (3.00 g, 12.1 mM) in dry ether at the room temperature, and the mixture was stirred for 12 h at the same temperature. The mixture was poured into ice water, and the mixture was extracted with ether. The extract was washed with saturated sodium hydrogen carbonate solution and brine, dried with magnesium sulfate, and concentrated in vacuo to give 4-(4-methylthiophenoxy)benzyl bromide (2.39 g, 64%) as colorless crystals, m.p. 32.9° C.

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe extract was washed with saturated sodium hydrogen carbonate solution and brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48f0ee2cca2246d888d4819119784d8e
Source dataset
uspto-grants-1993_04
Patent number
US05206259

Reaction notes

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