Water → HCID 4307534, compound

HRID 2054154Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-fluorobenzaldehyde (12.6 mmol, 1.57 g), 4-chlorobenzenethiol (12.6 mmol, 1.81 g), K2CO3 (15.1 mmol, 2.09 g) in DMF (5.00 mL) was heated at 90° C. for 10 h. After cooling to room temperature, the reaction mixture was poured into a separatory funnel with water (100 mL). The phases were separated and the aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with water (2×100 mL), brine (50 mL) and dried over MgSO4. Removal of the solvents in vacuo gave a light yellow liquid. Purification by flash column chromatography (eluent: 5% EtOAc in Hexane) provided 4-(4-chlorophenylthio)benzaldehyde (2.00 g, 76.0% yield) as a light yellow liquid. 1H NMR (CDCl3) δ 9.93 (s, 1H), 7.72 (d, J=8.3 Hz, 2H), 7.46-7.39 (m, 4H), 7.25 (d, J=8.3 Hz, 2H).

Workup

temperatureAfter cooling to room temperature
customThe phases were separated
extractionthe aqueous layer was extracted with CH2Cl2 (3×50 mL)
washThe combined organic layers were washed with water (2×100 mL), brine (50 mL)
dry with materialdried over MgSO4
customRemoval of the solvents in vacuo
customgave a light yellow liquid
customPurification by flash column chromatography (eluent: 5% EtOAc in Hexane)

Sources & evidence

ORD record: ord-b8ed01e7826c4962884d0548fee4ebde
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329656B2

Reaction notes

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