p-Xylyl bromide → HCID 3619668, compound

HRID 2221242Notes

Reaction equation

HRID 2221242 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH3:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:21]=[CH:20][C:17]([CH3:18])=[CH:16][CH:15]=1)[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 7721p-Xylyl bromideHCID 24758Sodium hydrideHCID 249055-Bromoindole

Product 1

HCID 3619668HCID 3619668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60%, 2.53 g, 63.1 mmol) was added portionwise to a stirring solution of 5-bromoindole (8.25 g, 42.1 mmol) in DMF (80 mL) at 0° C. under a nitrogen atmosphere over a period of 10 min. The mixture was then warmed up to room temperature. After the reaction mixture was stirred at room temperature for 1 hour, 4-methylbenzyl bromide (12.0 g, 63.1 mmol) was added and the mixture was stirred at room temperature overnight. The reaction was quenched with aqueous ammonium chloride and diluted with water. The aqueous phase was extracted with ethyl acetate. The organic extract was washed with water and brine, then dried over anhydrous magnesium sulfate. This mixture was concentrated to give a crude oil (14.1 g, 71%). Crystallization from petroleum ether afforded the title compound as a white solid, m.p: 56-57° C. Mass spectrum (APCI, [M+H]+) m/z 300. 1HNMR (400 MHz, DMSO-d6): δ 7.73 (s, 1H), 7.53 (s, 1H), 7.40 (d, 1H, J=8.9 Hz), 7.18 (d, 1H, J=10.5 Hz), 7.09 (d, 2H, J=8.2 Hz), 7.07 (d, 2H, J=8.2 Hz), 6.45 (s, 1H), 5.35 (s, 2H), and 2.22 ppm (s, 3H). Elemental Analysis for C16H14BrN: Calculated: C, 64.02; H, 4.70; N, 4.67. Found: C, 63.66; H, 4.59; N, 4.71.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction was quenched with aqueous ammonium chloride
  3. additiondiluted with water
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThis mixture was concentrated
  9. customto give a crude oil (14.1 g, 71%)
  10. customCrystallization from petroleum ether

Sources & evidence

ORD record
ord-5d8c406541274500a4e532ffef1037ea
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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