Phosphorus tribromide → 2-Benzyl benzylbromide

HRID 51379

Reaction equation

HRID 51379 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)(Cl)(Cl)Cl>[CH2:5]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][Br:2])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 741092-Benzylbenzyl alcohol

Product 1

HCID 124220982-Benzyl benzylbromideYield 99.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of phosphorus tribromide (2.1 mL, 6.0 g, 22.1 mM) in 30 mL of carbon tetrachloride was slowly added dropwise to solution of 2-benzylbenzyl alcohol (1.98 g, 10 mM) in 70 mL of carbon tetrachloride at 0° C. The mixture was stirred at 0° C. for 2 hours, then at room temperature for 2 hours. The solvent was removed in vacuo and the residue diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford 2.6 g (99%) of 2-benzylbenzyl bromide as a yellow solid. 1H NMR (DMSO-d6) δ7.5-7.0 (m, 9H), 4.7 (s, 2H), and 4.15 (s, 2H). IR (CDCl3, cm−1) 3065, 1601, 1495, and 1453. MS (FD) m/e 260, 262.

Workup

  1. waitat room temperature for 2 hours
  2. customThe solvent was removed in vacuo
  3. additionthe residue diluted with ethyl acetate and saturated aqueous sodium bicarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-14aa9a06b8124f568acf960fe3874cd4
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Linked notes

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