Benzyl Bromide → 9-Benzyl-6-fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 1057628

Reaction equation

HRID 1057628 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]2=1.CCCCC.[H-].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([N:11]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]=2[C:4]2[C:12]1=[CH:13][CH:14]=[C:2]([F:1])[CH:3]=2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8003PentaneHCID 24758Sodium hydrideHCID 3357046-fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 186716779-Benzyl-6-fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one (0.3938 g, 0.0019 mol) is added to a slurry of pentane-washed NaH (0.0970 g, 0.0024 mol) in DMF (3 mL) and after stirring for 10 min, benzyl bromide (0.28 mL, 0.0024 mol) is added. After stirring for 4 h at room temperature, the mixture is partitioned between water and ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated to dryness. The resulting solids are chromatographed on silica gel (200 mL) using dichloromethane/heptane (60/40 to 80/20 to 100/0) to give 0.3681 g (65%) of the title compound. An aliquot is recrystallized from ethyl acetate/heptane; MS (ESI+) for C19H16FNO m/z 294.2 (M+H)+; IR (drift) 1634, 1523, 1483, 1466, 1447, 1357, 1254, 1138, 900, 868, 803, 799, 759, 729, 700 cm−1; 1H NMR (CDCl3) δ2.22, 2.59, 2.88, 5.32, 6.95, 7.01, 7.15, 7.30, 7.96. Anal. Calcd for C19H16FNO: C, 77.80; H, 5.50; N, 4.78. Found: C, 77.65; H, 5.39; N, 4.69.

Workup

  1. stirringAfter stirring for 4 h at room temperature
  2. customthe mixture is partitioned between water and ethyl acetate
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe resulting solids are chromatographed on silica gel (200 mL)

Sources & evidence

ORD record
ord-c446ea19570a47c58cf2a976012a60af
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Linked notes

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