Water → HCID 23365443, compound

HRID 1080724Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([Sn](C)(C)C)=[CH:16][CH:15]=1.O>CN(C)C=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A vigorously stirred solution of 3.4 g (14 mmol) of 1-bromo-2-(2-thienyl)benzene and 3.77 g (15 mmol) of 4-methylphenyltrimethylstannane in 50 mL of dimethylformamide under a nitrogen atmosphere was treated with 427 mg of bis(triphenylphosphine) palladium(II) chloride and the resulting mixture heated at 100° C. for 4.5 hours. The reaction mixture was cooled, poured into 250 mL of water and the resultant mixture extracted with ethyl ether. The combined extracts were washed with water (4×), dried over magnesium sulfate and evaporated under vacuum. The residue was dissolved in hexane/ether (100:5) and chromatographed on silica gel, eluting with hexane/ether (100:5) to give 2.25 g of he product. 1H NMR (200 MHz, CDCl3): 2.33 (s, 3H), 6.48 (dd, 1H), 6.83 (dd, 1H), 7.08 (m, 4H), 7.16 (dd, 1H), 7.35 (m, 3H), 7.46 (dd, 1H).

Workup

temperatureThe reaction mixture was cooled
extractionthe resultant mixture extracted with ethyl ether
washThe combined extracts were washed with water (4×)
dry with materialdried over magnesium sulfate
customevaporated under vacuum
dissolutionThe residue was dissolved in hexane/ether (100:5)
customchromatographed on silica gel
washeluting with hexane/ether (100:5)
customto give 2.25 g of he product

Sources & evidence

ORD record: ord-40e172c4f1c4441f939ee3f7c1e7adb6
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05583130

Reaction notes

Loading…