4-Bromoaniline → HCID 178425043, compound

HRID 1466423Notes

Reaction equation

HRID 1466423 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[C:22]#[N:23]>C1COCC1>[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:22](=[NH:23])[C:21]2[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:20]=2[Cl:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 230532-Chloro-6-methylbenzonitrileHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 178425043HCID 178425043, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under N2 atmosphere at room temperature to a solution of lithium bis(trimethylsilyl)amide (9.7 mL, 1.0 M solution in THF, 9.7 mmol) was added a solution of 4-bromoaniline (1.67 g, 9.7 mmol) in 10 mL anhydrous THF. After the mixture was stirred at ambient temperature for 40 min, a solution of 2-chloro-6-methylbezonitrile (1.55 mg, 10.2 mmol) in 10 mL anhydrous THF was added. The reaction mixture was stirred at room temperature overnight, and then poured into 300 mL ice water. The orange precipitate was collected by filtration, washed with hexane and air dried to give a light orange solid (2.19 g, 66% yield), which was used directly for the next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. filtrationThe orange precipitate was collected by filtration
  3. washwashed with hexane and air
  4. customdried

Sources & evidence

ORD record
ord-36752399d0034a9d890161c69a3fce3e
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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