N,N'-Dimethylethylenediamine → benzene, 1-fluoro-3-(phenylsulfonyl)-

Temperature

90 °C

A mixture of 1-fluoro-3-iodobenzene (2.22 g, 10 mmol), sodium phenylsulfinate (2.16 g, 13 mmol), copper (1) trifluoromethylsulfonate-benzene complex (0.15 g, 0.3 mmol), N,N′-dimethylethylenediamine (0.95 g, 1.09 mmol) and dimethyl sulfoxide (20 mL) was heated at 90° C. under nitrogen with stirring for 2 h then at 115° C. for 18 h. Mixture was cooled then partitioned between water (150 mL) and 1:1 Et2O− EtOAc (100 mL) and the organic phase was washed with water (3×100 mL), dried (Na2SO4) and evaporated in vacuo to give a beige solid. Chromatography (SiO2; gradient elution with 0-40% Et2O in petrol) gave the title compound (1.725 g, 73%) as a colourless solid. 1H NMR (CDCl3): 8.02-7.93 (2H, m), 7.81-7.71 (1H, m), 7.71-7.46 (5H, m), 7.28 (1H, m).

1. waitat 115° C. for 18 h
2. temperatureMixture was cooled
3. customthen partitioned between water (150 mL) and 1:1 Et2O− EtOAc (100 mL)
4. washthe organic phase was washed with water (3×100 mL)
5. dry with materialdried (Na2SO4)
6. customevaporated in vacuo
7. customto give a beige solid
8. washChromatography (SiO2; gradient elution with 0-40% Et2O in petrol)

ORD record

ord-328193288a7c4dbfb3ec5fe8ee676cc7

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018214B2