Pyridine → 2-Phenylpropan-2-yl 2-bromoacetate

HRID 1841863Notes

Reaction equation

HRID 1841863 reaction equation
N1C=CC=CC=1.[Br:7][CH2:8][C:9](Br)=[O:10].[C:12]1([C:18]([OH:21])([CH3:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[Br:7][CH2:8][C:9]([O:21][C:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:20])[CH3:19])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 120532-Phenyl-2-propanolHCID 61147Bromoacetyl bromide

Product 1

HCID 538027202-Phenylpropan-2-yl 2-bromoacetateYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (3.84 mL, 47.7 mmol) followed by bromoacetyl bromide (4.16 mL, 47.7 mmol) was added to a solution of 2-phenylpropan-2-ol (5.00 g, 36.7 mmol) in dichloromethane (100 mL) at 0° C., warmed to r.t. and stirred overnight. The reaction mixture was washed with water (3×100 mL), saturated aqueous sodium bicarbonate (3×100 mL), water (2×100 mL), dried (Na2SO4) and concentrated. The crude residue was purified by silica gel flash column chromatography (neutralized with TEA, heptanes) to afford the title compound (2.8 g (non-optimized), 30%) as a colorless oil. 1H NMR (300 MHz, ((CD3)2CO) δ: 7.44 (d, J=7.2 Hz, 2H), 7.34 (t, J=7.2 Hz, 2H), 7.25 (t, J=7.2 Hz, 1H), 4.01 (s, 2H), 1.78 (s, 6H).

Workup

  1. washThe reaction mixture was washed with water (3×100 mL), saturated aqueous sodium bicarbonate (3×100 mL), water (2×100 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified by silica gel flash column chromatography (neutralized with TEA, heptanes)

Sources & evidence

ORD record
ord-2932121a8a844c23985f765d39edb11f
Source dataset
uspto-grants-2015_02
Patent number
US08945814B2

Reaction notes

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