반응 #1461060

반응 방정식

hydrochloric acid

6-bromo-1-chloro-naphthalen-2-ol

benzothiophene-2-boronic acid

potassium carbonate

→

6-benzo[b]thiophen-2-yl-1-chloro-naphthalen-2-ol

수율 23.9%

용매

water

THF

반응 조건

후처리

1. 1
   온도to cool to ambient temperature
2. 2
   추출It was extracted with chloroform
3. 3
   세척The organic phase was then washed with water and brine
4. 4
   건조It was dried with anhydrous magnesium sulfate
5. 5
   여과filtered
6. 6
   기타solvent evaporated
7. 7
   기타The residue was purified by flash chromatography
8. 8
   기타Drying at 60° C. in vacuo for 20 minutes

실험 절차

A mixture of 6-bromo-1-chloro-naphthalen-2-ol (11.2 g, 43.5 mmol), benzothiophene-2-boronic acid (15.1 g, 85.0 mmol) in three portions, palladium (II) acetate (0.76 g, 3.43 mmol) in three portions, potassium carbonate (30.1 g, 224 mmol) in three portions, tetrabutylammonium bromide (14.0 g, 43.5 mmol) in water (65 mL) and THF (40 mL) was heated at 70° C. for 8.5 hours. The reaction mixture was allowed to cool to ambient temperature and then poured into excess 2N hydrochloric acid. It was extracted with chloroform. The organic phase was then washed with water and brine. It was dried with anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified by flash chromatography using 100% chloroform, 30–50% 1,2-dichloroethane in hexane and 20–30% 1,2-dichloroethane in hexane (Biotage apparatus) eluent. Drying at 60° C. in vacuo for 20 minutes yielded 6-benzo[b]thiophen-2-yl-1-chloro-naphthalen-2-ol as a beige-yellow solid (3.22 g, 23.9%) MP: 220–1° C.; Mass spectrum (−ES, [M−H]−) m/z 309/311. 1H NMR (500 MHz, DMSO-d6): δ 10.64 (s, 1H), 8.26 (d, 1H, J=1.73 Hz), 8.11 (d, 1H, J=8.85 Hz), 8.05 (dd, 1H, J=8.85 and 1.83 Hz), 7.95–8.01 (m, 2H), 7.87–7.92 (m, 2H), 7.33–7.43 ppm (m, 3H). Elemental Analysis for C18H11ClOS: Calcd: C, 69.56; H, 3.57; N, 0.00; Found: C, 69.58; H, 3.83; N, 0.00.

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