Triethylamine → 2-Bromo-3,4-dimethoxybenzonitrile

HRID 1582382

Reaction equation

HRID 1582382 reaction equation
Cl.NO.C([N:6]([CH2:9][CH3:10])CC)C.[Br:11][C:12]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16]C=1C=O.CS(Cl)(=O)=O>C(#N)C>[Br:11][C:12]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][C:10]=1[C:9]#[N:6]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 6185382-Bromo-3,4-dimethoxybenzaldehyde

Product 1

HCID 227212152-Bromo-3,4-dimethoxybenzonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of hydroxylamine hydrochloride (1.42 g, 20. 4 mmol) and triethylamine (5.7 ml, 40.8 mmol) in acetonitrile (10 ml) was stirred at room temperature for 15 minutes before a solution of 2-bromo-3,4-dimethoxybenzaldehyde (5.0 g, 20.4 mmol) in acetonitrile (40 ml) was added over 40 minutes. The resulting mixture was stirred overnight before a fifth of the resulting solution was charged with methanesulfonyl chloride (0.74 ml, 10 mmol total) and triethylamine (0.6 ml, 4.3 mmol total) portionwise over 6 hours. The mixture was stirred overnight, quenched with water, extracted with ethyl acetate, dried over MgSO4 and concentrated in-vacuo to give 0.90 g of the subtitle product (93%).

Workup

  1. additionwas added over 40 minutes
  2. stirringThe mixture was stirred overnight
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-66f67991ab1245b8a7aca6ef96431ff1
Source dataset
uspto-grants-2004_05
Patent number
US06734303B2

Linked notes

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