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Pyridine → 1-(4-Chlorobenzo[b]thiophen-2-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-2-en-1-one

HRID 336999
Notes
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Reaction equation

HRID 336999 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11](=[O:27])[CH2:12][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)(O)[C:14]([F:17])([F:16])[F:15])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.O=S(Cl)Cl.N1C=CC=CC=1>C(Cl)Cl.[NH4+].[Cl-]>[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11](=[O:27])[CH:12]=[C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)[C:14]([F:15])([F:16])[F:17])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 866937461-(4-Chlorobenzo[b]thiophen-2-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one

Product 1

HCID 866937471-(4-Chlorobenzo[b]thiophen-2-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-2-en-1-oneYield 100%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 25517Ammonium ChlorideSolvent

Procedure

Stir a mixture of 1-(4-chlorobenzo[b]thiophen-2-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one (1.1 g, crude, 2.43 mmol), SOCl2 (1.16 g, 0.7 mL, 9.43 mmol) and pyridine (384 mg, 0.4 mL, 4.86 mmol) in anhydrous DCM (10 mL) at ambient temperature for overnight. Dilute the mixture with saturated NH4Cl solution and extract the aqueous mixture with DCM (10 mL×3). The combined organic layers are washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum to afford crude 1-(4-chlorobenzo[b]thiophen-2-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-2-en-1-one as brown solid (1.05 g, 100%). 1H NMR (400 MHz, CDCl3) 68.12-8.10 (s, 1H), 7.69-7.64 (m, 1H), 7.47-7.44 (m, 2H), 7.38-7.35 (m, 2H), 7.27-7.24 (m, 1H), 6.96-6.92 (s, 1H).

Workup

  1. extractionextract the aqueous mixture with DCM (10 mL×3)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-860cc490d4184e60a6add760a831ebbc
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889710B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes