Benzyl Bromide → HCID 18671682, compound

HRID 1057609Notes

Reaction equation

HRID 1057609 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[CH2:11][CH2:10][CH2:9][C:8](=[O:15])[C:7]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:13]1[C:12]2[CH2:11][CH2:10][CH2:9][C:8](=[O:15])[C:7]=2[C:6]2[C:14]1=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=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 221477458-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 18671682HCID 18671682, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one (2.23 g, 0.011 mol) is added to a slurry of pentane-washed NaH (0.59 g, 0.015 mol) in DMF (18 mL) and after stirring for 20 min, benzyl bromide (1.7 mL, 0.014 mol) is added. The mixture is stirred for 1 h at which time the mixture is partitioned between water and ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated to dryness. The resulting residue is chromatographed on silica gel (200 mL) using methanol/dichloromethane (1/99). The solids are then recrstallized from ethyl acetate/dichloromethane/hexane to give 2.25 g (70%) of the title compound; mp 183-184° C.; MS (ESI−) for C19H16FNO m/z 292.1 (M−H)−; IR (drift) 1639, 1631, 1495, 1459, 1434, 1359, 1246, 1219, 1193, 1125, 798, 789, 736, 730, 698 cm−1; 1H NMR (CDCl3) δ2.23, 2.58, 2.87, 5.51, 6.92, 7.03, 7.16, 7.29, 8.07. Anal. Calcd for C19H16FNO: C, 77.80; H, 5.50; N, 4.78. Found: C, 77.58; H, 5.59; N, 4.79.

Workup

  1. stirringThe mixture is stirred for 1 h at which time the mixture
  2. customis 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 residue is chromatographed on silica gel (200 mL)

Sources & evidence

ORD record
ord-1c81415ec12a4c8681716179b14c6885
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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