N-bromobutanimide → Methyl 6-bromo-7-fluoro-chromane-4-carboxylate

HRID 1021485Notes

Reaction equation

HRID 1021485 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[Br:16][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[F:1])[O:9][CH2:8][CH2:7][CH:6]2[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67080260methyl 7-fluoro-3,4-dihydro-2H-chromene-4-carboxylate

Product 1

HCID 46929189Methyl 6-bromo-7-fluoro-chromane-4-carboxylateYield 89.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 7-fluoro-3,4-dihydro-2H-chromene-4-carboxylate (336 mg, 1.60 mmol) was diluted with DMF (5 mL) followed by the addition of N-bromosuccinimide (313 mg, 1.76 mmol). The reaction was heated at 50° C. and stirred for 2.5 hours. The reaction was cooled, diluted with ethyl acetate and washed with water, saturated sodium bicarbonate, water, and brine. The organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a Biotage 40M cartridge, gradient 5% ethyl acetate/hexane to 50% to yield the title compound (415 mg, 89.8% yield).

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with water, saturated sodium bicarbonate, water, and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was purified

Sources & evidence

ORD record
ord-fa8d3b8ca1f0491fa54a9da15285ef2f
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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