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

HRID 1626381Notes

Reaction equation

HRID 1626381 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 magnesium sulfate, filtered and concentrated. The material was purified by silica gel chromatography 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 magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f70c04f147d14e85ada8130dfb7c7184
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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