1-Bromo-3-chlorobenzene → HCID 22117504, compound

HRID 1275747Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1.[CH:14]1[C:26]2[C:25](=[O:27])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]=2[CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>C(OCC)C>[Cl:13][C:9]1[CH:8]=[C:7]([C:25]2([OH:27])[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]3[C:26]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A 2.5M solution of butyllithium in hexanes (1.8 eq), (Aldrich) was added dropwise to a solution of 1-bromo-3-chlorobenzene (1.5 eq) in anhydrous diethyl ether with stirring under argon at -40° C. After stirring at room temperature for 0.5 h, a solution of 9-fluorenone (1 eq), (Aldrich) in anhydrous diethyl ether was added dropwise to the mixture with stirring and cooling at 0° C. The reaction mixture was stirred at room temperature for 1 h, poured into a saturated solution of ammonium chloride and extracted with dichloromethane. The combined dichloromethane extracts were washed with brine, dried (MgSO4), the solvent evaporated and the residue chromatographed on silica gel column with 10% ethyl acetate in hexanes to give the title compound as an oil.

Workup

stirringAfter stirring at room temperature for 0.5 h
stirringwith stirring
temperaturecooling at 0° C
stirringThe reaction mixture was stirred at room temperature for 1 h
extractionextracted with dichloromethane
washThe combined dichloromethane extracts were washed with brine
dry with materialdried (MgSO4)
customthe solvent evaporated
customthe residue chromatographed on silica gel column with 10% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-b43ca4290dc9431c941696e62f3840d4
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06162824

Reaction notes

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