Sodium Carbonate → HCID 69001230, compound

Temperature

100 °C

The product from Step F (1.90 g, 6.0 mmol) was dissolved in N,N-dimethylformamide (15 mL) and added sodium carbonate (3.25 g, 30.0 mmol) and heated to 100° C. for over 1.5 hours. The suspension was then stirred for 24 hours at room temperature. The reaction was filtered over sodium sulfate and rinsed with diethyl ether (50 mL). The filtrate was acidified to pH 1 with concentrated hydrochloride acid. The organic layer was washed (2×50 mL) with water, then extracted with 5% aqueous solution of potassium hydroxide (3×50 mL). The basic aqueous solution was acidified with concentrated hydrochloric acid and extracted (3×50 mL) with diethyl ether. The combined ether extracts were dried over sodium sulfate, filtered and concentrated to give 6-bromo-benzothiophen-7-ol (1.09 g, 77% crude) as a red-brown solid: 1H NMR (500 MHz, CDCl3) δ 7.45-7.42 (m, 2H), 7.31-7.29 (m, 2H), 5.93 (s, 1H).

1. filtrationThe reaction was filtered over sodium sulfate
2. washrinsed with diethyl ether (50 mL)
3. washThe organic layer was washed (2×50 mL) with water
4. extractionextracted with 5% aqueous solution of potassium hydroxide (3×50 mL)
5. extractionextracted (3×50 mL) with diethyl ether
6. dry with materialThe combined ether extracts were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-ece981c4f4b04632bede56722d399c59

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08227486B2