ChemicalBook CAS DataBase List 4-CHLORO-2-PHENYLBENZOFURAN

4-CHLORO-2-PHENYLBENZOFURAN synthesis

11synthesis methods

Product Name:4-CHLORO-2-PHENYLBENZOFURAN
CAS Number:344562-15-8
Molecular formula:C14H9ClO
Molecular Weight:228.67

Benzene, 1-methyl-4-[(2-phenylethynyl)sulfonyl]-

28995-88-2
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3-chlorophenyl diethylcarbamate(WXC07280)

159390-33-7
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344562-15-8
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Yield:344562-15-8 67%

Reaction Conditions:

Stage #1: 3-chlorophenyl N,N-diethylcarbamatewith sec.-butyllithium in tetrahydrofuran;cyclohexane at -78 - -65; for 1.58333 h;Inert atmosphere;
Stage #2: 1-methyl-4-((phenylethynyl)sulfonyl)benzene in tetrahydrofuran;cyclohexane at 20; for 0.5 h;Inert atmosphere;
Stage #3: with sodium hydroxide in dimethyl sulfoxide at 140; for 2 h;regioselective reaction;

Steps:

General procedure

General procedure: A solution of starting carbamate 1 (1 mmol) in THF (2 mL) at-78 C under nitrogen atmosphere was treated with a solution of s-BuLi (0.85 mL of a 1.4 Msolution in cyclohexane, 1.2 mmol). The reaction mixture was allowed to reach -65 C for5 min (-70 C for 4-substituted carbamates 1o-q) and was stirred at this temperature for90 min. Then, the corresponding alkynylsulfone (1.3 mmol) was added, and the resultingsolution was allowed to warm to room temperature and was then stirred for 30 min.The solvents were removed under reduced pressure and the crude solution was treatedwith NaOH (2 mmol, 80 mg) in DMA (2 mL) or DMSO (2 mL). The resulting solutionwas warmed by conventional heating (Method A: DMSO, 140 C) or under microwaveirradiation (Method B: DMA, 160 C), and stirred at this temperature until the completionof the reaction (see Table 3). The mixture was diluted with EtOAc and NH4Cl (aq), and thelayers were separated. The aqueous phase was extracted with EtOAc (3 10 mL), and thecombined organic layers were dried over anhydrous Na2SO4. The solvents were removedunder reduced pressure, and the residue was purified by silica gel column chromatography(hexane/EtOAc), affording the 2-arylbenzo[b]furans 3 and 4.

References:

Feberero, Claudia;Renedo, Lorena;Sanz, Roberto;Sedano, Carlos;Suárez-Pantiga, Samuel;Virumbrales, Cintia [Molecules,2022,vol. 27,# 2,art. no. 525]

858854-82-7 Synthesis