Sodium Chloride → 3-bromo-4,5-dimethoxybenzonitrile

HRID 870517Notes

Reaction equation

HRID 870517 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[CH:5]=O.C([O-])=O.[Na+].Cl.[NH2:19]O.[Cl-].[Na+]>C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[C:5]#[N:19]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium Formate

Product 1

HCID 7355263-bromo-4,5-dimethoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
95 °C

Procedure

11 g 3-Bromo-4,5-dimethoxybenzaldehyde, 6.5 g sodium formate were dissolved in 50 mL of formic acid and stirred at 95° C. 3.6 g Hydroxylamine hydrochloride was added in portions and the mixture stirred for 4 h at 95° C., 2 days at 50° C. and 3 h at 120° C. The mixture was poured on to 700 mL of an almost saturated sodium chloride solution/ice mixture and the precipitate isolated, washed with water and dried to provide 3-bromo-4,5 dimethoxybenzonitrile.

Workup

  1. stirringthe mixture stirred for 4 h at 95° C., 2 days at 50° C. and 3 h at 120° C
  2. customthe precipitate isolated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0c3cbabf0ad2414cbdad1a14d25ca7c3
Source dataset
uspto-grants-2015_03
Patent number
US08969568B2

Reaction notes

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