Thiophosgene → HCID 90415948, compound

Temperature

7.5 °C

3,5-Difluorobenzene-1,2-diol (670 mg, 4.6 mmol) was stirred in dry chloroform (8 mL), treated with thiophosgene (580 mg, 5.0 mmol), cooled to 5-10° C., and treated dropwise with 10% NaOH solution (4.2 g, 11 mmol) over 45 min. After 30 min, the volatiles were removed by rotary evaporation and the residual solid was collected by filtration and washed with water. The solid was dissolved in ethyl acetate (30 mL), washed with water (2×20 mL), washed with saturated NaCl (1×10 mL), dried (Na2SO4), and evaporated. The residue was purified by chromatography on silica with a 0-20% ethyl acetate-hexane gradient to give the title compound (710 mg, 82%): 1H NMR (400 MHz, CDCl3) δ 6.95 (ddd, J=6.8, 2.3, 1.4 Hz, 1H), 6.89 (td, J=9.5, 2.3 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −109.99 (s), −127.93 (s); EIMS m/z 188.

1. customthe volatiles were removed by rotary evaporation
2. filtrationthe residual solid was collected by filtration
3. washwashed with water
4. dissolutionThe solid was dissolved in ethyl acetate (30 mL)
5. washwashed with water (2×20 mL)
6. washwashed with saturated NaCl (1×10 mL)
7. dry with materialdried (Na2SO4)
8. customevaporated
9. customThe residue was purified by chromatography on silica with a 0-20% ethyl acetate-hexane gradient

ORD record

ord-58e9fbce5d0640a88daeba31d5d7ee8e

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149038B2