Iodine → HCID 9962290, compound

HRID 2260875Notes

Reaction equation

HRID 2260875 reaction equation
[I:1]I.[CH2:3]([S:10]/[C:11](/[Sn](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[CH:12]\[CH:13]=[C:14](/[S:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)\[Sn:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(Cl)Cl>[CH2:3]([S:10]/[C:11](/[I:1])=[CH:12]\[CH:13]=[C:14](/[S:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)\[Sn:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 807IodineHCID 10985908HCID 10985908, compound

Product 1

HCID 9962290HCID 9962290, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Iodine (56 mg, 0.22 mmol) in CH2Cl2 (10 mL) was added over a period of 2 h at 0° C. to 4 (200 mg, 0.20 mmol) in CH2Cl2 (20 mL) under argon. Analysis by TLC (1:2 CH2Cl2 :hexanes) indicated the disappearance of 4. The solution was slowly warmed to room temperature and then washed with NaHSO3 (2×25 mL) and KF solution (1×25 mL), dried (MgSO4), concentrated in vacuo and the residue purified by flash column chromatography (1:6 CH2Cl2 :hexanes) to afford 5 as a pale yellow oil (0.15 g, yield 97%): 1H NMR δ 6.6-7.8 (m, 27 H), 3.78 (s, 2 H), 3.75 (s, 2 H); 13C NMR δ 127-146 (several), 42.24, 40.46; Anal. Calcd for C36H31IS2Sn, C, 55.91; H, 4.04. Found, C, 56.12; H, 4.19.

Workup

  1. washwashed with NaHSO3 (2×25 mL) and KF solution (1×25 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash column chromatography (1:6 CH2Cl2 :hexanes)

Sources & evidence

ORD record
ord-cf629fc43e2b45e2b22ce3885697d5e1
Source dataset
uspto-grants-1995_12
Patent number
US05478959

Reaction notes

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