Dimethylformamide → 5-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

HRID 1943238Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[F:12].[Li]CCCC.CN([CH:21]=[O:22])C>C1COCC1>[F:12][C:3]1[C:4]2[O:9][CH2:8][CH2:7][O:6][C:5]=2[CH:10]=[CH:11][C:2]=1[CH:21]=[O:22]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 6-bromo-5-fluoro-2,3-dihydro-1,4-benzodioxin (146 mg, 0.627 mmol) in THF (5 ml) at −78° C. was treated with n-BuLi (0.551 ml, 1.378 mmol) under a nitrogen atmosphere and stirred at −78° C. for 15 min before treatment with a solution of DMF (0.243 ml, 3.13 mmol) in THF) (2.00 ml). The reaction was stirred for 10 min at −78° C. and then the reaction was allowed warm to rt over 10 min and stirred at rt for 0.5 h. Reaction was treated with 2M HCl (20 ml) and extracted with ethyl acetate (3×100 ml). The organic extracts were evaporated, dried (MgSO4), filtered, evaporated, chromatographed (0-100% EtOAC:Cyclohexane) to give product as a white solid (25 mg, 22%).

Workup

temperaturethe reaction was allowed warm to rt over 10 min
stirringstirred at rt for 0.5 h
customReaction
extractionextracted with ethyl acetate (3×100 ml)
customThe organic extracts were evaporated
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated
customchromatographed (0-100% EtOAC:Cyclohexane)

Sources & evidence

ORD record: ord-6c56a9e2edb34fceaa0c6566e8b08525
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389524B2

Reaction notes

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