Ethyl Bromide → HCID 22722354, compound

HRID 1581736Notes

Reaction equation

HRID 1581736 reaction equation
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[C:3]1[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C:4]=1[NH:5]2.O1[CH2:21][CH2:20]OC1.CC([O-])(C)C.[K+].C(Br)C.[NH4+].[Cl-]>O>[CH2:20]([N:5]1[C:6]2[C:2](=[CH:1][CH:9]=[CH:8][CH:7]=2)[C:3]2[C:16]3[C:11]([CH2:10][C:4]1=2)=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH3:21]

Participants

7

Reactant 5

HCID 6332Ethyl BromideHCID 125861,3-DioxolaneHCID 25517Ammonium ChlorideHCID 131294105,6-Dihydroindeno[2,1-b]indoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 22722354HCID 22722354, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.00 g of 5,6-dihydroindeno[2,1-b]indole (99.8% by G.C., Mw=205.26, 73.1 mmol) were dissolved into 200 mL of 1,3-dioxolane (Aldrich) at room temperature in a 0.5-L flask. 8.28 g of t-BuOK (Fluka, 99%, Mw=112.22, 73.1 mmol) were added and the reaction mixture turned from a green suspension to a brown solution. After 30 min stirring at room temperature, 5.51 mL of EtBr (Fluka, 99%, Mw=108.97, d=1.46, 73.1 mmol) were added, obtaining a brown suspension. Stirring was continued for 2 hours, then the reaction mixture was poured into water containing 8 g of NH4Cl (Carlo Erba RPE, purity 99.5%). After two hours stirring, the green-brown suspension was filtered on a G4 frit, the solid dried in air under moderate vacuum to give a green powder (8.98 g), which was analyzed by 1H NMR. Purity 98.9% wt. by 1H NMR (yield=52.1%).

Workup

  1. customobtaining a brown suspension
  2. stirringStirring
  3. waitwas continued for 2 hours
  4. stirringAfter two hours stirring
  5. filtrationthe green-brown suspension was filtered on a G4 frit
  6. customthe solid dried in air under moderate vacuum

Sources & evidence

ORD record
ord-a58373c8f96441a7ad88aa989795e76c
Source dataset
uspto-grants-2004_05
Patent number
US06730754B2

Reaction notes

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