Allyl bromide → HCID 19702682, compound

HRID 861274Notes

Reaction equation

HRID 861274 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[CH2:10](Br)[CH:11]=[CH2:12]>CN1C(=O)CCC1>[CH2:10]([N:2]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)[CH3:1])[CH:11]=[CH2:12]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 108205133-(Methylamino)phenol

Product 1

HCID 19702682HCID 19702682, compoundYield 137.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To 3-(N-methylamino)phenol (10 g, 80 mmol), dissolved in 80 ml of NMP, was added allyl bromide (9.8 ml, 113 mmol) via syringe. The yellow solution was heated to 80° C. for 4 hours. The reaction mixture was poured into distilled water (200 ml) and saturated aqueous sodium bicarbonate solution was added. Extraction with diethyl ether (3×200 ml), drying over anhydrous magnesium sulfate, filtration and concentration vacuo yielded 18.0 g of 3-(N-allyl-N-methylamino)phenol as a viscous green tinted oil. Vacuum distillation at 1 torr (110°-120° C.) yielded 10.5 g (80%) as a pale yellow oil.

Workup

  1. additionThe reaction mixture was poured
  2. distillationinto distilled water (200 ml) and saturated aqueous sodium bicarbonate solution
  3. additionwas added
  4. extractionExtraction with diethyl ether (3×200 ml)
  5. dry with materialdrying over anhydrous magnesium sulfate, filtration and concentration vacuo

Sources & evidence

ORD record
ord-f790b9028eb141a094fa59af618c3370
Source dataset
uspto-grants-1998_02
Patent number
US05714304

Reaction notes

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