Toluene → 3-Fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl

HRID 1648344Notes

Reaction equation

[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Br[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([F:28])[CH:22]=1.C1(C)C=CC=CC=1>C(O)C>[C:1]([NH:5][S:6]([C:9]1[C:10]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([F:28])[CH:22]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a vigorously stirred solution of 4.27 g (16.6 mmol) of 2-(N-t-butylsulfamoyl)phenylboronic acid (from Step D), 32 mmol (26 mL of a 1.25N aqueous solution) of NaOH in 40 mL of ethanol was added 1.89 g (10 mmol, 1.27 mL) of 4-bromo-2-fluorotoluene, 60 mL of toluene, and 289 mg (0.25 mmol) of tetrakis(tfiphenylphosphine)palladium. The mixture was stirred at 90° C. for 4.5 h, cooled to room temperature, and the volatiles were removed in vacuo. The residue was extracted with ethyl acetate (3×) and the combined organic layers were washed with water, brine, and dried (Na2SO4). The crude product obtained after filtration and removal of solvents was flash chromatographed over silica gel (elution with hexane-EtOAc) to afford 2.96 g (92%) of the desired product cleanly (TLC in 4:1 hexane-EtOAc) as an off-white foam; mass spectrum (FAB) m/e 322 (M+1)+.

Workup

temperaturecooled to room temperature
customthe volatiles were removed in vacuo
extractionThe residue was extracted with ethyl acetate (3×)
washthe combined organic layers were washed with water, brine
dry with materialdried (Na2SO4)
customThe crude product obtained
filtrationafter filtration and removal of solvents
customchromatographed over silica gel (elution with hexane-EtOAc)

Sources & evidence

ORD record: ord-d5197fc3e7dc48139f1137338a5a24b7
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05436259

Reaction notes

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