Ethyl 2-fluoro-3-((4-methoxybenzyl)thio)benzoate → Ethyl 2-fluoro-3-mercaptobenzoate
Reaction equation
[F:1][C:2]1[C:12]([S:13]CC2C=CC(OC)=CC=2)=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[C:12]([SH:13])=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of compound 3 (30.0 g, 93.75 mmol) in TFA (54.5 mL) was heated to 80° C. and stirred for 12 h under inert atmosphere. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed under reduced pressure. The residue was dissolved in ice-cold water (100 mL), basified with solid sodium bicarbonate and extracted with EtOAc (2×200 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. This was purified by silica gel column chromatography using 3% EtOAc/Hexanes to afford compound A (11.7 g, 62%) as a pale brown syrup. 1H NMR (500 MHz, CDCl3): δ 7.70-7.66 (m, 1H), 7.48-7.44 (m, 1H), 7.08-7.04 (m, 1H), 4.20 (q, J=7.5 Hz, 2H), 3.67 (s, 1H), 1.40 (t, J=7.5 Hz, 3H); LC-MS (ESI): 91.8%; m/z 199.0 (M−H+); (column: X Select CSH C-18, 50×3.0 mm, 3.5 μm); RT 2.60 min; 5 mM NH4OAc: ACN; 0.8 mL/min).
Workup
- customafter completion of the reaction
- customthe volatiles were removed under reduced pressure
- dissolutionThe residue was dissolved in ice-cold water (100 mL)
- extractionextracted with EtOAc (2×200 mL)
- dry with materialThe combined organic extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customto obtain the crude
- customThis was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-99d6abcc20e543b1bbb4e2815714de78
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09334261B2
Reaction notes
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