1,2-Dichloroethane → 3-Bromo-2-methylbenzamide

HRID 908296Notes

Reaction equation

HRID 908296 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].C(Cl)CCl.C1C=[N:20]C2N(O)N=NC=2C=1.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:20])=[O:6]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 588288773-Bromo-2-methylbenzamideYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-bromo-2-methylbenzoic acid (5.00 g, 23.3 mmol) was dissolved in DMF (41.6 ml) and EDC (5.46 g, 28.5 mmol), HOAt (3.97 g, 29.2 mmol), ammonium chloride (4.90 g, 90.9 mmol), and diisopropylethylamine (12.5 ml, 71.8 mmol) were added. The reaction was stirred at room temperature over the weekend, and then poured into water (100 ml). The resultant precipitate was filtered, washed with water, collected, and dried under vacuum to give the title compound (4.63 g, 93%). MS (ESI pos. ion) m/z: 214 (M+H). Calc'd Exact Mass for C8H8BrNO: 213.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. washwashed with water
  3. customcollected
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8eebe4f5f8764a9d874a5ff3414c742a
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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