Toluene → Benzeneacetonitrile, 2,3-dichloro-

HRID 418374

Reaction equation

HRID 418374 reaction equation
Cl.NC(N)=N.C[O-].[Na+].C1(C)C=CC=CC=1.[Cl:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[C:24](=C(OCC)CF)[C:25]#[N:26]>CO>[Cl:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:24][C:25]#[N:26]

Participants

6

Reactant 4

HCID 1140TolueneHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 543953282-(2,3-Dichlorophenyl)-3-ethoxy-4-fluoro-2-butenenitrile

Product 1

HCID 229020Benzeneacetonitrile, 2,3-dichloro-Yield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To guanidine hydrochloride (25.4 kg, 266 mole) in methanol (60 litres) was added 30% w/w sodium methoxide in methanol solution (49.2 kg, 273.3 mole). The suspension was heated to 55° C.±2° C. The toluene solution of 2-(2,3-dichlorophenyl)-3-ethoxy-4-fluoro-2-butenenitrile was added over a period of 45 minutes and the resultant mixture was boiled under reflux for 4 hours, cooled then quenched into water (230 litres). The solid precipitate was washed with 5 portions of methanol (25 litres) to yield the racemate as an off white solid (26.3 kg, 38% yield from 2,3-dichlorophenylacetonitrile).

Workup

  1. temperatureThe suspension was heated to 55° C.±2° C
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. customthen quenched into water (230 litres)
  5. washThe solid precipitate was washed with 5 portions of methanol (25 litres)

Sources & evidence

ORD record
ord-59ccc84137fc44f3bbafa9eb91f1ac1a
Source dataset
uspto-grants-2012_01
Patent number
US08093268B2

Linked notes

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