Benzyl Bromide → HCID 67359429, compound

HRID 1664489Notes

Reaction equation

HRID 1664489 reaction equation
[Cl: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][CH:9]([C:15]([OH:17])=[O:16])[CH2:8][C:7]2=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C.O>[CH2:24]([O:16][C:15]([CH:9]1[CH2:8][C:7]2[C:6]3[C:14](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=3)[NH:13][C:12]=2[CH2:11][CH2:10]1)=[O:17])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 67360248HCID 67360248, compound

Product 1

HCID 67359429HCID 67359429, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A stirred mixture of crude 8-chloro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid (4.45 g, 17.8 mmol) and cesium carbonate (2.90 g, 8.92 mmol) in ethanol (150 ml) and water (25 ml) is refluxed until a clear solution is obtained (15 min). Then the solvents are evaporated and the dried residue is dissolved in dry DMF. This solution is treated with benzylbromide (2.27 ml, 18.7 mmol) and stirred at 45° C. for 15 min. The resulting precipitate is filtered off and the filtrate is concentrated. The residue is purified by flash chromatography on silica gel (heptane/EtOAc 3:1) to deliver pure title compound as a yellowish solid (4.2 g) in 69% yield. tR (LC-5) 1.09 min; ESI-MS (positive ion): m/z 340.19 [M+H]+ (calcd 339.82 for C20H18NO2Cl). 1H-NMR (DMSO-d6): 1.90 (m, 1H); 2.19 (m, 1H); 2.86 (m, 5H); 5.13 (s, 2H); 6.91 (t, J=7.6 Hz, 1H); 7.04 (d, J=7.6 Hz, 1H); 7.32 (m, 6H); 11.0 (br s, 1H).

Workup

  1. temperatureis refluxed until a clear solution
  2. customis obtained (15 min)
  3. customThen the solvents are evaporated
  4. dissolutionthe dried residue is dissolved in dry DMF
  5. filtrationThe resulting precipitate is filtered off
  6. concentrationthe filtrate is concentrated
  7. customThe residue is purified by flash chromatography on silica gel (heptane/EtOAc 3:1)
  8. custom1.09 min

Sources & evidence

ORD record
ord-9a326d0a2e85453e9db52a6bfe3c9ec5
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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