Phenacyl bromide → 2-(3-Bromo-2-methylphenylamino)-1-phenylethanone

HRID 661898Notes

Reaction equation

HRID 661898 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(=O)(O)[O-].[Na+].Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18]>C(#N)C>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 1235383-Bromo-o-toluidineHCID 516892Sodium Bicarbonate

Product 1

HCID 666069472-(3-Bromo-2-methylphenylamino)-1-phenylethanoneYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Step 1 A mixture of 3-bromo-2-methylaniline (0.620 mL, 5.03 mmol) and sodium bicarbonate (565 mg, 6.73 mmol) in acetonitrile (4.5 mL) was treated with 2-bromo-1-phenylethanone (500 mg, 2.51 mmol) and the mixture was stirred at rt. After 24 h, the suspension was filtered and the precipitate was suspended and sonicated in water, collected again by filtration, washed with water and dried to provide 2-(3-bromo-2-methylphenylamino)-1-phenylethanone as an off-white solid (508 mg, 67%). 1H NMR (400 MHz, chloroform-d) 68.00-8.06 (2H, m), 7.61-7.68 (1H, m), 7.53 (2H, t, J=7.6 Hz), 6.94-7.01 (2H, m), 6.51-6.58 (1H, m), 5.06 (1H, t, J=4.1 Hz), 4.62 (2H, d, J=4.4 Hz), 2.40 (3H, s). Mass spectrum m/z 304, 306 (M+H)+.

Workup

  1. filtrationthe suspension was filtered
  2. customsonicated in water
  3. filtrationcollected again by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-524824aa942349638f47f3d54d80c5ac
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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