4-Morpholinecarbonyl chloride → (6-Fluoro-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-morpholin-4-yl-methanone

HRID 2184133Notes

Reaction equation

Br[C:2]1[C:22]([F:23])=[CH:21][C:5]2[O:6][C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.C([Li])CCC.[N:29]1([C:35](Cl)=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C(=O)(O)[O-].[Na+]>C(OCC)C>[F:23][C:22]1[C:2]([C:35]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:36])=[CH:3][C:4]2[O:8][C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:6][C:5]=2[CH:21]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a cooled (−78° C.) solution of 5-bromo-6-fluoro-2,2-diphenyl-benzo[1,3]dioxole (17.59 g, 47.4 mmol) in diethyl ether (300 mL) was slowly added a solution of n-butyl lithium in hexanes (1.6M, 30 mL, 48 mmol, 1.0 eq.). The reaction mixture was stirred 1 h at −78° C. before the addition of 4-morpholinecarbonylchloride (8.5 g, 56.9 mmol, 1.2 eq.). The reaction mixture was allowed to warm to 20° C. and poured into an aqueous solution of sodium bicarbonate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine. Volatiles were removed in vacuo. Purification by flash chromatography afforded the title compound (13.0 g, 68%) as a light yellow solid.

Workup

extractionThe aqueous layer was extracted with ethyl acetate
washThe combined organic layers were washed with brine
customVolatiles were removed in vacuo
customPurification by flash chromatography

Sources & evidence

ORD record: ord-be95a293843d43c3ae722ce60659a270
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900227B2

Reaction notes

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