Phosphorus tribromide → HCID 15291211, compound

HRID 375089Notes

Reaction equation

HRID 375089 reaction equation
[C:1]([N:4]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]O)=[CH:8][CH:7]=1)[CH3:5])(=[O:3])[CH3:2].P(Br)(Br)[Br:15]>C(Cl)Cl>[C:1]([N:4]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10][Br:15])=[CH:8][CH:7]=1)[CH3:5])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 54439979N-[4-(Hydroxymethyl)phenyl]-N-methylacetamide

Product 1

HCID 15291211HCID 15291211, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(N-acetyl-N-methylamino)benzyl alcohol (543.0 mg, 3.0 mmol), prepared as in step 2, dissolved in dry CH2Cl2 (11.5 mL) was added dropwise 1M PBr3 in CH2Cl2 (3.6 mL, 3.6 mmol) at 0° C. The reaction was stirred at ambient temperature until TLC indicated complete reaction (~5 hours). The resulting solution was partitioned between ethyl acetate and brine. The combined organic layers were decolorized with charcoal, dried (MgSO4), filtered through celite and concentrated in vacuo. Purification by flash chromatography on silica gel (40% ethyl acetate/hexane) provided 4-(N-acetyl-N-methylamino)benzyl bromide as a colorless solid (595 mg, 81.0%). 1H NMR (300 MHz, CDCl3) δ7.46 (2H, d, J=8.5 Hz), 7.18 (2H, d, J=8.5 Hz), 4.50 (2H, s), 3.27 (3H, s), 1.88 (3H, br s). MS m/e 242 (M+H)+, 259/261 (M+NH4)+. Analysis calc'd for C10H12NOBr: C, 49.61; H, 5.00; N, 5.79. Found: C, 49.35; H, 4.97; N, 5.65.

Workup

  1. customreaction (~5 hours)
  2. customThe resulting solution was partitioned between ethyl acetate and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered through celite and
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0496722f836b439792c5716c61f918f6
Source dataset
uspto-grants-1996_01
Patent number
US05484786

Reaction notes

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