Ammonia → 3,6-Dibromo-9-(prop-2-yn-1-yl)-9H-carbazole

HRID 1252531Notes

Reaction equation

HRID 1252531 reaction equation
[NH2-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3.N.[CH2:19](Br)[C:20]#[CH:21]>C1(C)C=CC=CC=1>[CH2:21]([N:8]1[C:7]2[CH:6]=[CH:5][C:4]([Br:3])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([Br:17])[CH:13]=2)[C:20]#[CH:19]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 7842Propargyl bromideHCID 24533Sodium amideHCID 2748743,6-Dibromocarbazole

Product 1

HCID 155440993,6-Dibromo-9-(prop-2-yn-1-yl)-9H-carbazoleYield 63.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium amide (7.73 g, 0.198 mole) was carefully added to a suspension of 3,6-dibromocarbazole (54.7 g, 0.168 mole) in liquid ammonia (ca. 600 ml.) under argon atmosphere. After solution occurred, propargyl bromide (20.2 g, 0.170 mole) in toluene was added dropwise to the solution over 25 minute period. The reaction mixture was stirred for an additional 100 minutes, and the ammonia was allowed to evaporate. The resultant solid was washed with water and recrystallized from ethanol to give 39 g (63% yield) tan needles, mp 193°-194°. This solid gave an infrared spectrum with significant features at 3290, 2120, 870, 830, 800, and 790 cm-1.

Workup

  1. customto evaporate
  2. washThe resultant solid was washed with water
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4b076ea6987341b283b0816bd6d202a6
Source dataset
uspto-grants-1988_05
Patent number
US04743659

Reaction notes

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