Dichloromethane → HCID 22065777, compound

HRID 1828615Notes

Reaction equation

HRID 1828615 reaction equation
[I:1]Cl.C[Si](C)(C)[C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18]4[CH:30]=[CH:29][C:28]5[C:27]6[C:22](=[CH:23][C:24]([C:31]7[CH:43]=[CH:42][C:41]8[C:40]9[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=9)[C:34]([CH2:47][CH2:48][CH3:49])([CH2:44][CH2:45][CH3:46])[C:33]=8[CH:32]=7)=[CH:25][CH:26]=6)[C:21]([CH2:53][CH2:54][CH3:55])([CH2:50][CH2:51][CH3:52])[C:20]=5[CH:19]=4)=[CH:12][CH:13]=3)[C:8]([CH2:61][CH:62]([CH3:65])[CH2:63][CH3:64])([CH2:56][CH:57]([CH3:60])[CH2:58][CH3:59])[C:7]=2[CH:6]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>C(Cl)(Cl)(Cl)Cl>[I:1][C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18]4[CH:30]=[CH:29][C:28]5[C:27]6[C:22](=[CH:23][C:24]([C:31]7[CH:43]=[CH:42][C:41]8[C:40]9[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=9)[C:34]([CH2:47][CH2:48][CH3:49])([CH2:44][CH2:45][CH3:46])[C:33]=8[CH:32]=7)=[CH:25][CH:26]=6)[C:21]([CH2:53][CH2:54][CH3:55])([CH2:50][CH2:51][CH3:52])[C:20]=5[CH:19]=4)=[CH:12][CH:13]=3)[C:8]([CH2:61][CH:62]([CH3:65])[CH2:63][CH3:64])([CH2:56][CH:57]([CH3:60])[CH2:58][CH3:59])[C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 24640Iodine chlorideHCID 22065810HCID 22065810, compound

Product 1

HCID 22065777HCID 22065777, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

ICl (1.0 M in methylene chloride, 2.80 ml, 2.80 mmol) is added dropwise to a solution of 2-trimethylsilyl-9,9-bis(2-methylbutyl)-9′,9′,9″,9″-tetrakis(n-propyl)-7,2′;7′,2″-terfluorene (13a) (2.45 g, 2.80 mmol) in CCl4 (15 ml) at 0° C. After stirring for 30 min, the reaction mixture is poured into a Na2CO3 aqueous solution (5 wt %) with vigorous stirring until discoloration for extraction with methylene chloride. The organic extracts are washed with brine before dried over MgSO4. Upon evaporating off the solvent, the residue is washed with ethanol to yield 2-iodo-9,9-bis(2-methylbutyl)-9′,9′,9″,9″-tetrakis(n-propyl)-7,2′;7′,2″-terfluorene (14a) (2.36 g, 91%) as a light yellow solid.

Workup

  1. washThe organic extracts are washed with brine
  2. dry with materialbefore dried over MgSO4
  3. customUpon evaporating off the solvent
  4. washthe residue is washed with ethanol

Sources & evidence

ORD record
ord-74c72cd54b6045f18084e0de1844c095
Source dataset
uspto-grants-2006_06
Patent number
US07057009B2

Reaction notes

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