Triethylamine → 3-Chloro-4-fluorobenzo[b]thiophene-7-carbonitrile

HRID 470909Notes

Reaction equation

HRID 470909 reaction equation
C(N(CC)CC)C.Cl[CH:9]1[S:13][C:12]2[C:14]([C:19]#[N:20])=[CH:15][CH:16]=[C:17]([F:18])[C:11]=2[CH:10]1[Cl:21]>ClCCl>[Cl:21][C:10]1[C:11]2[C:17]([F:18])=[CH:16][CH:15]=[C:14]([C:19]#[N:20])[C:12]=2[S:13][CH:9]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 685468432,3-Dichloro-4-fluoro-2,3-dihydrobenzo[b]thiophene-7-carbonitrile

Product 1

HCID 685494863-Chloro-4-fluorobenzo[b]thiophene-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.70 mL, 12.2 mmol) was added to a solution of 2,3-dichloro-4-fluoro-2,3-dihydrobenzo[b]thiophene-7-carbonitrile (1.57 g, 5.93 mmol) in dichloromethane (50 mL). The mixture was stirred at room temperature for 7 days, then the solvent was removed and the residue extracted with EtOAc. The organic extracts were then washed with water, brine and dried over Na2SO4. After removal of the solvent, the residue was purified by silica gel column chromatography to give 3-chloro-4-fluorobenzo[b]thiophene-7-carbonitrile as a white solid (1.19 g, 95% for two steps). 1H NMR (400 MHz, CDCl3, δ in ppm) 7.73 (dd, J=4.1, 8.2 Hz, 1H), 7.42 (s, 1H), 7.17 (dd, J=8.2, 10.5 Hz, 1H).

Workup

  1. customthe solvent was removed
  2. extractionthe residue extracted with EtOAc
  3. washThe organic extracts were then washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customAfter removal of the solvent
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f27a086f367b451a8a47bbb36a950ada
Source dataset
uspto-grants-2014_01
Patent number
US08629167B2

Reaction notes

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