Phosphorus tribromide → HCID 15291211, compound

HRID 439824Notes

Reaction equation

HRID 439824 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. dissolutiondissolved
  2. customreaction (~5 hours)
  3. customThe resulting solution was partitioned between ethyl acetate and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through celite and
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (40% ethyl acetate / hexane)

Sources & evidence

ORD record
ord-9c0ca0be71be47cfa5554753523101fb
Source dataset
uspto-grants-1996_05
Patent number
US05516795

Reaction notes

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