Toluene → Biphenyl-3-yl(3,4,5-trimethoxyphenyl)sulfane

HRID 63211

반응식

HRID 63211 반응식
CC(C)([O-])C.[Na+].CO[C:9]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=1.I[C:17]1[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=1.[C:29]1(C)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>[Cu](I)I>[C:14]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:9]=[CH:10][CH:11]=[C:12]([S:15][C:17]2[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=2)[CH:13]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 127654-MethoxybenzenethiolHCID 2981335-Iodo-1,2,3-trimethoxybenzeneHCID 23676156Sodium t-butoxide

생성물 1

HCID 53363791Biphenyl-3-yl(3,4,5-trimethoxyphenyl)sulfane

시약·촉매·용매 1

HCID 83717Copper iodide촉매

반응 조건

온도
110 °C

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. customAfter the reaction vessel was sealed
  2. customPurification
  3. customan amorphous solid was obtained (40% yield)

출처 및 근거

ORD 기록
ord-9ce2fd2b16764bb6995d19bbe3e98d6b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447049B2

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