3,4-Dichlorobenzaldehyde → HCID 22101839, compound

HRID 727249Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:16]=[O:17].C(=O)([O-])O.[Na+]>C(OCC)C>[Cl:12][C:13]1[CH:14]=[C:15]([CH:16]([C:4]2[S:3][CH:2]=[N:6][CH:5]=2)[OH:17])[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Bromothiazole (5 g) in dry diethyl ether (20 ml) was added dropwise to a stirred solution of n-butyllithium (1.6M in hexanes, 21 ml) in diethyl ether (20 ml) at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, trimethylsilylchlorlde (3.9 ml) was added and the mixture was allowed to warm to 0° C. The mixture was then cooled to -70° C. and further n-butyllithium (21 ml) was added. The mixture was warmed to 0° C. and after 30 minutes was cooled again to -70° C. and 3,4-dichlorobenzaldehyde (5.8 g) in diethyl ether (40 ml) was added. The mixture was then allowed to warm to room temperature and after 30 minutes saturated aqueous sodium hydrogen carbonate was added. The mixture was extracted with dichloromethane and the material thus obtained was purified by chromatography on silica gel to give the title compound. The hydrochloride salt was prepared. M.p. 167°-170° C.

Workup

additiontrimethylsilylchlorlde (3.9 ml) was added
temperatureThe mixture was then cooled to -70° C.
temperatureThe mixture was warmed to 0° C. and after 30 minutes
temperaturewas cooled again to -70° C.
additionwas added
extractionThe mixture was extracted with dichloromethane
customthe material thus obtained
customwas purified by chromatography on silica gel

Sources & evidence

ORD record: ord-d59c97b7719a48c5ae33033070e6000f
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712299

Reaction notes

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