Phenol → 4-(3-(N-methylsulfamoyl)phenyloxy)benzene

Participants

Role	Name	HCID	Charge
Reactant	Phenol	HCID 996	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	3-bromo-N-methylbenzene-1-sulfonamide	HCID 7213265	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(3-(N-methylsulfamoyl)phenyloxy)benzene	HCID 23614573	11.4%

Reaction Steps

To a slurry of phenol (1.9 g, 20 mmol), K2CO3 (6.0 g, 40 mmol), and CuI (4 g, 20 mmol) in DMF (25 mL) was added N-methyl-3-bromobenzenesulfonamide (2.5 g, 10 mmol), and the resulting mixture was stirred at the reflux temp. overnight, cooled to room temp., and separated between EtOAc (50 mL) and a 1 N HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2×50 mL). The combined organic phases were sequentially washed with water (2×50 mL) and a saturated NaCl solution (50 mL), dried (MgSO4), and concentrated under reduced pressure. The residual oil was purified by column chromatography (30% EtOAc/70% hexane) to give 4-(3-(N-methylsulfamoyl)phenyloxy)benzene (0.30 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07528255B2
Source dataset	uspto-grants-2009_05
ORD ID	ord-bb3221a5b45847e9bbd75cc282e66e0c
Source note	uspto-grants-2009_05