Potassium Carbonate → HCID 23001837, compound

HRID 398090Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[OH:11][C:12]1[CH:13]=[CH:14][C:15]2[S:19][CH2:18][CH2:17][C:16]=2[CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:13]=[CH:14][C:15]3[S:19][CH2:18][CH2:17][C:16]=3[CH:20]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-bromo-2-fluorobenzaldehyde (1.08 g, 5.32 mmol), 5-hydroxy-2,3-dihydrobenzothiophene (prepared as described in Synth. Commun. 1991, 21, 959-964) (808 mg, 5.31 mmol) and K2CO3 (1.47 g, 10.6 mmol) in DMF (5 mL) was heated at 90° C. for 16 h. After cooling to room temperature the mixture was partitioned between water (50 mL) and ether (50 mL), the aqueous layer being extracted with ether (50 mL). The combined organic extracts were washed with water (50 mL), dried (MgSO4) and evaporated. The residue was purified by column chromatography [SiO2; 9:1 (pentane/EtOAc)], then triturated with ether, to give the product (1.1 g, 62%) as a pale yellow solid; δH (CDCl3, 400 MHz) 3.28 (2H, t), 3.41 (2H, t), 6.78 (1H, d), 6.84 (1H, d), 6.92 (1H, s), 7.20 (1H, d), 7.58 (1H, d), 8.00 (1H, s), 10.43 (1H, s).

Workup

temperatureAfter cooling to room temperature the mixture
customwas partitioned between water (50 mL) and ether (50 mL)
extractionthe aqueous layer being extracted with ether (50 mL)
washThe combined organic extracts were washed with water (50 mL)
dry with materialdried (MgSO4)
customevaporated
customThe residue was purified by column chromatography [SiO2; 9:1 (pentane/EtOAc)]
customtriturated with ether

Sources & evidence

ORD record: ord-ee49d599641040919758821b012e0af9
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610747B2

Reaction notes

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