Toluene → HCID 10664097, compound

HRID 1522716Notes

Reaction equation

HRID 1522716 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1.Br[CH2:18][CH2:19][CH3:20].[C:21]1(C)[CH:26]=CC=C[CH:22]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:18]([C:7]1([CH2:22][CH2:21][CH3:26])[C:6]2[CH:5]=[C:4]([Br:3])[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 1140TolueneHCID 78401-BromopropaneHCID 143362-Bromo-9H-fluoreneHCID 14798Sodium Hydroxide

Product 1

HCID 10664097HCID 10664097, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
50 °C

Procedure

50% Aqueous sodium hydroxide (500 mL) was added to a solution of 2-bromofluorene (52.8 g, 215 mmol) and tetrabutylammonium bromide (3.47 g, 10.8 mmol) in toluene (500 mL), and heated to 50° C. After 90 minutes 1-bromopropane (60 mL, 650 mmol) was added, and the solution stirred at 50° C. for 16 hours. The organic layer was separated, washed with water (2×500 mL), brine (500 mL), dried over magnesium sulfate, and the solvent removed. Recrystallisation from a dichloromethane/methanol mixture gave (7) (51.5 g, 73%).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (2×500 mL), brine (500 mL)
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed
  5. customRecrystallisation from a dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-c440b719c0cd4eb5a7b173cf01130c9b
Source dataset
uspto-grants-2015_07
Patent number
US09078330B2

Reaction notes

Loading…