Hydrochloric Acid → HCID 54420298, compound

HRID 262211Notes

Reaction equation

HRID 262211 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:16][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1.[N:22]1C=CC=C[CH:23]=1.Cl>C(Cl)(Cl)Cl>[C:23]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:16][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1)#[N:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 54486270HCID 54486270, compound

Product 1

HCID 54420298HCID 54420298, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 40 g. of cuprous cyanide and 99 g. (0.29 mole) of methyl 3-(4-bromophenyl)benzofuran-5-acetate in 30 ml. of pyridine is heated at 160°-175° C. under a nitrogen atmosphere for 20 hours, cooled to about 100° C., and then a solution of 200 g. of ferric chloride, 100 ml. of concentrated hydrochloric acid and 200 ml. of ice water is added. To this mixture is added 300 ml. of chloroform, and stirring is continued for one hour. The solid is separated by filtration and washed with chloroform. The filtrate and washings are combined, dried, then evaporated to provide a residue which is recrystallized from an N,N-dimethylformamide-water mixture to provide methyl 3-(4-cyanophenyl)-benzofuran-5-acetate.

Workup

  1. additionA stirred mixture of 40 g
  2. additionTo this mixture is added 300 ml
  3. customThe solid is separated by filtration
  4. washwashed with chloroform
  5. customdried
  6. customevaporated
  7. customto provide a residue which
  8. customis recrystallized from an N,N-dimethylformamide-water mixture

Sources & evidence

ORD record
ord-0b8ba41d191f432a88caa2728bf4c4e8
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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