Phosphorus tribromide → 2-(2-Bromomethylphenylsulfanylmethyl)benzene

HRID 11311

Reaction equation

HRID 11311 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:18]>CCOCC>[Br:18][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 10977293[2-(Benzylsulfanyl)phenyl]methanol

Product 1

HCID 108808892-(2-Bromomethylphenylsulfanylmethyl)benzeneYield 62.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (2-Benzylsulfanyl)methanol 4 (120 mg, 0.522 mmol) in anhydrous Et2O was cooled to 4° C. A solution of PBr3 (49 μL, 0.52 mmol) in anhydrous Et2O was added dropwise, keeping the temperature below 10° C. The reaction was allowed to warm to ambient temperature and stirred for one hour. The reaction was filtered through silica gel (2.0 g) and washed with Et2O. The filtrate was washed with H2O saturated aqueous sodium bicarbonate and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give 95 mg of the named product as a yellow oil.

Workup

  1. customthe temperature below 10° C
  2. filtrationThe reaction was filtered through silica gel (2.0 g)
  3. washwashed with Et2O
  4. washThe filtrate was washed with H2O saturated aqueous sodium bicarbonate and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-dae2fd9bf2a242829a417f449efb103f
Source dataset
uspto-grants-2006_08
Patent number
US07098223B2

Linked notes

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