Water → 4-Fluoro-1-benzothiophene
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
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
- temperatureto cool
- extractionThe product was extracted with hexane (2×20 mL)
- washwashed with 1N HCl (100 mL) and 1N NaOH (50 mL)
- dry with materialdried over Na2SO4
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-2598a0fc07214e719019d641221fc41a
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056873B2
Reaction notes
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