Water → 1-methoxy-3-(phenylethynyl)benzene

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Phenylacetylene	HCID 10821	—
Reactant	3-Chloroanisole	HCID 17833	—
Catalyst	Sodium 2'-(dicyclohexylphosphino)-2,6-diisopropyl-[1,1'-biphenyl]-4-sulfonate	HCID 23674066	—
Solvent	Acetonitrile	HCID 6342	—
Product	1-methoxy-3-(phenylethynyl)benzene	HCID 11401525	95.1%

Reaction Steps

The general procedure described in Example 27 was used with 3-chloroanisole (0.063 mL, 0.50 mmol), phenylacetylene (0.072 mL, 0.65 mmol), PdCl2(CH3CN)2 (3.2 mg, 0.0125 mmol, 1.25 mol %), sodium 2′-(dicyclohexyl-phosphanyl)-2,6-diisopropyl-biphenyl-4-sulfonate (20.0 mg, 0.0375 mmol, 3.75 mol %), Cs2CO3 (650 mg, 2.00 mmol), water (1.0 mL), acetonitrile (1.5 mL), 12 h, 100° C. The product was isolated as a white solid (99 mg, 95%). Mp=70° C. (lit. 72-74° C.). 1H NMR (400 MHz, CDCl3) δ: 7.62 (m, 2H), 7.41 (m, 3H), 7.32 (t, 1H, J=7.6 Hz), 7.23 (dt, 1H, J=1.2 Hz, 7.6 Hz), 7.15 (m, 1H), 6.96 (qd, 1H, J=1.2 Hz, 2.4 Hz, 7.6 Hz). 13C NMR (125 MHz, CDCl3) δ: 159.5, 131.8, 129.6, 128.5, 128.48, 124.4, 124.3, 123.3, 116.5, 115.1, 89.5, 89.4, 55.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08735630B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-8b80cdcdfd7e43f2b654782bb6828792
Source note	uspto-grants-2014_05