Iodine chloride → HCID 68649267, compound

HRID 570900Notes

Reaction equation

HRID 570900 reaction equation
[I:1]Cl.[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([C:15]3[CH:27]=[CH:26][C:25]4[C:24]5[C:19](=[CH:20][C:21]([Si](C)(C)C)=[CH:22][CH:23]=5)[C:18]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:17]=4[CH:16]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>CO.ClCCl>[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([C:15]3[CH:27]=[CH:26][C:25]4[C:24]5[C:19](=[CH:20][C:21]([I:1])=[CH:22][CH:23]=5)[C:18]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:17]=4[CH:16]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 24640Iodine chlorideHCID 68649323HCID 68649323, compound

Product 1

HCID 68649267HCID 68649267, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.5 ml of an 1.0 M ICl solution in MeOH was slowly added to a solution of 500 mg (0.813 mmol) of 2-(6-p-pyridyl-phenyl)-7-trimethylsilyl-9,9-dioctylfluorene in 5 mL of dichloromethane. The resulting darkred solution was stirred for 2 h at room temperature after which the reaction mixture was quenched with a large excess of a Na2S2O3 in water. The mixture was extracted with water, and the organic fraction was dried using MgSO4 and the solvents were removed under reduced pressure. The product was purified using flash column chromatography (dichloromethane: Rf: 0.36). 450 mg (85%) product was obtained as a highly blue fluorescent, colourless solid material. 1H NMR (250 MHz, CDCl3): δ=8.73 (d, 3J=4.7 Hz, 1H; CH—N), 8.12 (d, 3J=8.5 Hz, 2H; CH—C—C(CH)—N), 7.80-7.73 (mp, 4H, ArH), 7.68 (s, 2H, ArH), 7.65 (d, 3J=5.0 Hz, 2H; CH—CH—N), 7.60 (s, 2H; ArH), 7.48 (d, 1H; 3J=8.4 Hz; ArH), 2.05-1.94 (mp, 4H; CH2—C), 1.05-1.25 (mp, 20H, CH2), 0.81 (t, 3J=6.6 Hz, 6H; CH3), 0.70 (br m, 4H, CH2). 13C{1H} NMR (500 MHz, CDCl3): δ=157.0 (CN), 153.4, 150.9 (C—C—CH2), 149.8 (CH—N), 142.0, 140.4, 140.0, 139.6, 138.2 (ArC), 136.8 (CH—CH—CH—N), 135.9, 132.1 (C—CI), 127.5, 127.3, 126.1, 122.1, 121.5, 121.3, 120.4, 120.1 (CH), 92.6 (CI), 55.5 (C—CH2), 40.2 (C—CH2), 31.7, 29.9, 29.2, 29.1 (CH2), 23.7 (C—CH2—CH2), 22.6 (CH3—CH2), 14.1 (CH3). Exact Mass (IE) m/z: 669.2825 [M]+ (calcd. 669.2832) fractions: 543.6 (m; [M-I]+), 318.4 (m; [M-(C8H17)—I]+). C40H48IN: calcd. C, 71.74; H, 7.22; N, 2.09. found C, 72.34; H, 7.20; N, 2.12.

Workup

  1. customwas quenched with a large excess of a Na2S2O3 in water
  2. extractionThe mixture was extracted with water
  3. customthe organic fraction was dried
  4. customthe solvents were removed under reduced pressure
  5. customThe product was purified

Sources & evidence

ORD record
ord-a5a60276c01a47d6aa04fbe6d5c20578
Source dataset
uspto-grants-2015_05
Patent number
US09023978B2

Reaction notes

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