Benzyl Bromide → alpha,alpha-Dimethyl-2-(phenylmethoxy)-benzeneacetamide

HRID 1697329

Reaction equation

HRID 1697329 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:13])([CH3:12])[C:9]([NH2:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.O>[CH3:12][C:8]([CH3:13])([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]([NH2:11])=[O:10]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 866632482-Hydroxy-alpha,alpha-dimethyl-benzeneacetamide

Product 1

HCID 66689021alpha,alpha-Dimethyl-2-(phenylmethoxy)-benzeneacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-hydroxy-α,α-dimethyl-benzeneacetamide (Example 198b, 15.34 g) dissolved in DMF (150 mL) was treated with potassium carbonate (11.83 g) and benzyl bromide (10.18 mL) under nitrogen. The resulting mixture was stirred at 25° C. for 16 h. The reaction mixture was diluted with water (500 mL) and stirred for 30 min. The solid was filtered off and washed with water and dried in vacuo to afford the subtitle compound (19.45 g).

Workup

  1. stirringstirred for 30 min
  2. filtrationThe solid was filtered off
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2e0f020fdd0549f7be6baa99dfd7806f
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Linked notes

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