Benzyl Bromide → HCID 18671670, compound

HRID 1057622Notes

Reaction equation

HRID 1057622 reaction equation
[Cl: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]([Cl: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 3357036-Chloro-4-oxo-1,2,3,4-tetrahydrocarbazole

Product 1

HCID 18671670HCID 18671670, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-1,2,3,9-tetrahydro-4H-carbazol-4-one (0.4010 g, 0.0018 mol) is added to a slurry of pentane-washed NaH (0.0902 g, 0.0023 mol) in DMF (2 mL) and after stirring for 27 min, benzyl bromide (0.26 mL, 0.0022 mol) is added. After stirring for 2.5 h at room temperature, the mixture is partitioned between aq. sodium bicarbonate 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 and 100/0) to give 0.5158 g (91%) of the title compound. An aliquot (0.0625 g) is recrystallized from ethyl acetate/heptane to give 0.0415 g of product; mp 196.5-197° C.; MS (ESI+) for C19H16ClNO m/z 310.1 (M+H)+; 1H NMR (CDCl3) δ2.24, 2.58, 2.87, 5.31, 6.99, 7.16, 7.29, 8.28. Anal. Calcd for C19H16ClNO: C, 73.66; H, 5.20; N, 4.52. Found: C, 73.18; H, 5.19; N, 4.58.

Workup

  1. stirringAfter stirring for 2.5 h at room temperature
  2. customthe mixture is partitioned between aq. sodium bicarbonate 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-5bfec81885fb4c3e9bba7abe69dbb426
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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