Sodium Carbonate → 1-(3-Phenylbenzo[b]thiophen-2-yl)ethanone

HRID 2036596Notes

Reaction equation

[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2[S:14][C:15]=1[C:16](=[O:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([C:11]2[C:12]3[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=3[S:14][C:15]=2[C:16](=[O:18])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of trans-dichlorobis(triphenyl-phosphine)palladium (ii) (0.138 g, 0.196 mmol), phenylboronic acid (0.717 g, 5.88 mmol), 1-(3-bromobenzo[b]thiophen-2-yl)ethanone (0.50 g, 1.960 mmol) and 2.0 N aqueous sodium carbonate (2.94 mL, 5.88 mmol) in Toluene (10 mL) was purged with nitrogen and heated to 110° C. overnight. After 16 h, the reaction mixture was partitioned between EtOAc and water. The organic layer was stirred over MgSO4, filtered and concentrated under reduced pressure to give a red oil. The product was purified by column chromatography on a silica gel column using 20 to 40% gradient of EtOAc in hexane as eluent to give 1-(3-phenylbenzo[b]thiophen-2-yl)ethanone a colorless oil: 1H NMR (400 MHz, CDCl3) δ 2.12 (s, 3H) 7.30-7.35 (m, 1H) 7.38-7.42 (m, 2H) 7.42-7.49 (m, 2H) 7.52-7.58 (m, 3H) 7.87 (d, J=8.2 Hz, 1H); LC-MS (ESI)] m/z 253.1 [M+H]+.

Workup

customwas purged with nitrogen
customthe reaction mixture was partitioned between EtOAc and water
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a red oil
customThe product was purified by column chromatography on a silica gel column

Sources & evidence

ORD record: ord-2946059c1320458a8b1035af880944c3
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575183B2

Reaction notes

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