Nitric Acid → 3-Bromo-4-methoxyphenylacetonitrile

HRID 1632048Notes

Reaction equation

HRID 1632048 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[K+].[Br-:13].[N+]([O-])(O)=O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC(Cl)C.ClCCl>[Br:13][C:4]1[CH:5]=[C:6]([CH2:9][C:10]#[N:11])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

7

Reactant 3

HCID 944Nitric AcidHCID 66031Benzeneacetonitrile, 4-methoxy-HCID 253877Potassium Bromide

Product 1

HCID 5226553-Bromo-4-methoxyphenylacetonitrileYield 70%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of compound 4-methoxyphenyl acetonitrile (5.88 g, 40 mmol), KBr (9.52 g, 80 mmol), tetrabutylammonium chloride (332 mg, 1.2 mmol) in dichloroethane (80 mL), was added 21% w/w nitric acid (48 g, 160 mmol). The reaction mixture was stirred at rt for 20 h, diluted with dichloromethane (80 mL) and washed with sat. NaHCO3 aq. (2×50 mL), water (2×50 mL), brine and dried over Na2SO4. After removal of solvent under vacuum, the residue was triturated with Et2O (10 ml)/hexanes (40 ml) to give 6.32 g of product; Yield: 70%.

Workup

  1. washwashed with sat. NaHCO3 aq. (2×50 mL), water (2×50 mL), brine
  2. dry with materialdried over Na2SO4
  3. customAfter removal of solvent under vacuum
  4. customthe residue was triturated with Et2O (10 ml)/hexanes (40 ml)

Sources & evidence

ORD record
ord-8fe94d73b08d4708be5d13ab6ce56acc
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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