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

HRID 1811079Notes

Reaction equation

HRID 1811079 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) δ8.00-8.06 (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-4532341990b042ac93a956f01d04e9b9
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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