N-bromobutanimide → methyl 6-bromo-7-fluoro-2,2-dimethyl-3,4-dihydro-2H-chromene-4-carboxylate

HRID 510601Notes

Reaction equation

HRID 510601 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:14]([O:16][CH3:17])=[O:15])[CH2:7][C:8]([CH3:13])([CH3:12])[O:9]2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[Br:18][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[F:1])[O:9][C:8]([CH3:13])([CH3:12])[CH2:7][CH:6]2[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67080255HCID 67080255, compound

Product 1

HCID 67080243methyl 6-bromo-7-fluoro-2,2-dimethyl-3,4-dihydro-2H-chromene-4-carboxylateYield 93.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 7-fluoro-2,2-dimethyl-3,4-dihydro-2H-chromene-4-carboxylate (187 mg, 0.785 mmol) was diluted with DMF (5 mL) followed by the addition of N-bromosuccinimide (154 mg, 0.863 mmol). The reaction was heated at 50° C. 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 (232 mg, 93.2% 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-43a8351c3dd04aadacb70902337a17bb
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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