Ammonium Chloride → HCID 65920453, compound

HRID 2041899Notes

Reaction equation

Br[C:2]1[C:3]([F:9])=[C:4]([F:8])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[C:15]([N:22]1[CH2:25][C:24](=[O:26])[CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[Cl-].[NH4+]>C(OCC)C>[F:9][C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[C:24]1([OH:26])[CH2:23][N:22]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:25]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3-bromo-1,2-difluorobenzene (2.3 g, 11.8 mmol) in dry diethylether (20 ml) at −78° C., under nitrogen was added n-butyllithium (2.5 M in hexane, 4.7 ml, 11.8 mmol) dropwise. The mixture was stirred for 1 h after which a solution of 1-Boc-3-azetidinone (2.0 g, 11.7 mmol) in dry diethyl ether (20 mL) was added dropwise. The resulting mixture was stirred at −78° C. for 15 min and then brought to ambient temperature and stirred for 2 h. Aqueous ammonium chloride (50 mL, 50%) and diethylether was added, the organic phase was collected and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1:4 to 1:1) to give the title compound (1.9 g). MS m/z (rel. intensity, 70 eV) 285 (M+, 1), 156 (55), 141 (69), 127 (bp), 57 (88).

Workup

additionwas added dropwise
custombrought to ambient temperature
stirringstirred for 2 h
customthe organic phase was collected
extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
dry with materialThe combined organic phase was dried (Na2SO4)
filtrationfiltered
customevaporated to dryness
customThe crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1:4 to 1:1)

Sources & evidence

ORD record: ord-0a9e9d8d98aa43e080a9d1f4de461681
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586572B2

Reaction notes

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