Ethyl 2-fluoro-3-((4-methoxybenzyl)thio)benzoate → Ethyl 2-fluoro-3-mercaptobenzoate

HRID 522770ノート

反応式

HRID 522770 の反応式
[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]

参加物

3

反応物 1

HCID 66764575Ethyl 2-fluoro-3-((4-methoxybenzyl)thio)benzoate

生成物 1

HCID 66765235Ethyl 2-fluoro-3-mercaptobenzoate収率 62.3%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

A stirred solution of compound A3 (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. The crude was purified through silica gel column chromatography using 3% EtOAc/Hexanes to afford compound 6 (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).

後処理

  1. customafter completion of the reaction
  2. customthe volatiles were removed under reduced pressure
  3. dissolutionThe residue was dissolved in ice-cold water (100 mL)
  4. extractionextracted with EtOAc (2×200 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto obtain the crude
  9. customThe crude was purified through silica gel column chromatography

出典と根拠

ORDレコード
ord-ffcef4a7a2b643ad82e6a910237dbbac
出典データセット
uspto-grants-2016_05
特許番号
US09334261B2

反応ノート

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