1,2-Dichloroethane → 3-Bromo-4-methylbenzamide

HRID 908294Notes

Reaction equation

HRID 908294 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[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[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH2:20])=[O:6]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 821303-Bromo-4-methylbenzoic acidHCID 181649HOAt

Product 1

HCID 6810613-Bromo-4-methylbenzamideYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

3-bromo-4-methylbenzoic acid (3.12 g, 14.5 mmol) was dissolved in DMF (26 ml) and EDC (3.51 g, 18.3 mmol), HOAt (2.79 g, 20.5 mmol), ammonium chloride (3.05 g, 57.0 mmol), and diisopropylethylamine (7.5 ml, 43.1 mmol) were added. The reaction was stirred at room temperature over the weekend, and then poured into water (100 ml), and diluted with more water. The resultant precipitate was filtered, washed with water, collected as a solution in EtOAc, and concentrated to give title compound (858.7 mg, 28%). 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 as a solution in EtOAc
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9f26a52d8fdc4d339138beb8b39821ac
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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