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Hydrochloric Acid → 5-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-carbaldehyde

HRID 1899095
Notes
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Reaction equation

HRID 1899095 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][CH:15]=[CH:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:9][CH:8]=1.CN(C)[CH:30]=[O:31].Cl>CCCCCC.O1CCCC1>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]([CH:30]=[O:31])=[CH:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:11][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 103368732-(4-Fluorophenyl)-3-(4-methylsulfonylphenyl)thiopheneHCID 178418339Butyllithium

Product 1

HCID 233727175-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8058HexaneSolvent

Procedure

n-Butyl lithium (1.6M) in hexane (36 ml) was added dropwise to a stirred solution of 2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (8.0 g) in tetrahydrofuran (80 ml) at -60° C. The mixture was stirred for 30 minutes, and N,N-dimethylformamide (3.7 ml) was added dropwise over ten minutes to the mixture. The mixture was stirred at -70° to -20° C. for 2 hours. 1N Hydrochloric acid (70 ml) was added dropwise, and the solution was extracted with ethyl acetate. The extract was washed with brine, dried and concentrated. The residual syrup was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (9:1). The obtained crystals (4.5 g) were recrystallized from ethyl acetate to give pale yellow crystals of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-carbaldehyde (3.7 g).

Workup

  1. stirringThe mixture was stirred at -70° to -20° C. for 2 hours
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residual syrup was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (9:1)
  7. customThe obtained crystals (4.5 g) were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-21d2f5d7bd6344f9ac86c9e8e8a86324
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05571810

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes