Acetyl chloride → N-(5-Bromo-2-methylphenyl)acetamide

HRID 2252226Notes

Reaction equation

HRID 2252226 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:6]([CH3:9])=[CH:7][CH:8]=1)[NH2:5].[C:10](Cl)(=[O:12])[CH3:11]>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:4]([NH:5][C:10](=[O:12])[CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 27348055-Bromo-o-toluidine

Product 1

HCID 14233594N-(5-Bromo-2-methylphenyl)acetamideYield 61.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-bromo-6-methylaniline (1.00 g , 5.37 mmol) in pyridine (8 mL) was added acetyl chloride (0.76 mL, 10.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 hour and concentrated. The residue was extracted with EtOAc, washed with 5% citric acid, dried over MgSO4, concentrated, and triturated with ether to give 0.750 g (61%) of the desired product as off-white crystal. MS (DCI/NH3) m/z: 227.9 (M+H)+, 229.9 (M+2+H)+; 1H NMR (300 MHz, CDCl3) δ 2.21 (s, 6H), 6.90 (m, 1H), 7.04 (d, J=8.14 Hz, 1H), 7.20 (d, J=7.80 Hz, 1H), 8.06 (s, 1H).

Workup

  1. concentrationconcentrated
  2. extractionThe residue was extracted with EtOAc
  3. washwashed with 5% citric acid
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customtriturated with ether

Sources & evidence

ORD record
ord-e9d63830102f421d8627628774a234b7
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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