Potassium Hydroxide → [1,1'-Biphenyl]-3-thiol

HRID 70037

반응식

HRID 70037 반응식
C([S:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)(=S)OCC.[OH-].[K+]>C(O)C>[C:9]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]=[CH:11][CH:12]=[C:7]([SH:6])[CH:8]=1

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 10540302S-Biphenyl-3-yl O-ethyl carbonodithioate

생성물 1

HCID 10821418[1,1'-Biphenyl]-3-thiol수율 113.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 52a (1.1 g, crude compound) in ethanol (8 mL) was added potassium hydroxide (2.1 g, 12 mL) and heated to reflux for overnight. The solution was cooled to RT and the ethanol was evaporated under reduced pressure. The residue was dissolved in water and washed with diethyl ether (10 mL). The aqueous layer was acidified with 2 N HCl and extracted with diethyl ether (3×50 mL). The organic extracts were washed with water (50 mL), brine (50 mL), dried over MgSO4, filtered and evaporated under reduced pressure to afford 0.85 g (77.3%) of crude biphenyl-3-thiol product (overall, 3 steps). Into a round-bottomed flask, stirred magnetically, were placed 0.1 g (1.04 mmol) of sodium tert-butoxide and 83 mg of copper iodide (0.43 mmol). After the reaction vessel was sealed, 0.13 g (0.71 mmol) of 4-methoxybenzenethiol and 0.19 g (0.65 mmol) of 5-iodo-1,2,3-trimethoxybenzene in 3.0 mL of toluene were injected through the septum. The reaction mixture was heated for overnight at 110° C. Purification was performed by flash chromatography, and an amorphous solid was obtained (40% yield). 1H NMR (500 MHz, CDCl3) δ 7.54-7.52 (m, 3H), 7.44-7.41 (m, 3H), 7.37-7.33 (m, 2H), 7.23 (s, br, 1H), 6.69 (s, 2H), 3.86 (s, 3H), 3.80 (s, 6H). MS (ESI) m/z 353.2 (M+H)+.

후처리

  1. temperatureheated
  2. temperatureto reflux for overnight
  3. customthe ethanol was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. washwashed with diethyl ether (10 mL)
  6. extractionextracted with diethyl ether (3×50 mL)
  7. washThe organic extracts were washed with water (50 mL), brine (50 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-a3f302f1333f4568978ba07145a2808c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822513B2

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