Boron trifluoride etherate → HCID 62791926, compound

HRID 2076071Notes

Reaction equation

C([Li])CCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10]C.Br[C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[Cl:20].B(F)(F)F.CC[O:27][CH2:28][CH3:29].[Cl-].[NH4+]>C(OCC)C.O>[Cl:20][C:14]1[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=1[CH:10]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:29][CH:28]1[OH:27]

Participants

Conditions

Temperature: -30 °C

Procedure

1.6 N Butyllithium-hexane solution (12.5 mL, 20 mmol) was added at −75° C. over 15 min to a solution of 2-bromo-1,4-dichloro-benzene (4.52 g, 20 mmol) in diethyl ether (50 mL). After stirring for 5 min, 8-oxa-bicyclo[5.10]octane (2.25 g, 20 mmol) was added, and subsequently, boron trifluoride etherate (2.51 mL, 20 mmol) was added dropwise over 0.5 h to the reaction mixture. Stirring was continued for 0.5 h at −75° C. The temperature was then raised to −30° C. and saturated aqueous ammonium chloride solution was added. After being stirred for 5 min, the mixture was diluted with water. The organic layer was separated, washed with water, and dried over sodium sulfate. Solvents were removed under reduced pressure and the remaining oil was purified by column chromatography on silica gel using heptane/0-20% ethyl acetate as eluent to give the title compound (3.55 g, 68%) as a pale-yellow oil. MS EI (m/e): 258.1 [(M)+].

Workup

stirringStirring
waitwas continued for 0.5 h at −75° C
stirringAfter being stirred for 5 min
customThe organic layer was separated
washwashed with water
dry with materialdried over sodium sulfate
customSolvents were removed under reduced pressure
customthe remaining oil was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-fc690f57d5654c42aea530378fbff671
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923450B2

Reaction notes

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