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Water → 4-Fluorobenzo[b]thiophene

HRID 2173026
Notes
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Reaction equation

HRID 2173026 reaction equation
[F:1][C:2]1[C:10]2[CH:9]=[C:8](C(O)=O)[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.O>CC(N(C)C)=O>[F:1][C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7378554-Fluoro-1-benzothiophene-2-carboxylic acid

Product 1

HCID 190880174-Fluorobenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
200 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Procedure

A mixture of 4-fluorobenzo[b]thiophene-2-carboxylic acid (200 mg, 1.019 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.457 mL, 3.06 mmol) in DMA (1 mL) was heated at 200° C. for 1 hour. The reaction mixture was allowed to cool and was poured into water (100 mL). The product was extracted with hexane (2×20 mL) and washed with 1N HCl (100 mL) and 1N NaOH (50 mL). The organic layers were combined, dried over Na2SO4 and the solvent was removed in vacuo to give the title compound as a yellow oil, which was used without further purification.

Workup

  1. temperatureto cool
  2. extractionThe product was extracted with hexane (2×20 mL)
  3. washwashed with 1N HCl (100 mL) and 1N NaOH (50 mL)
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2598a0fc07214e719019d641221fc41a
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09056873B2

Reaction notes

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