Iodine → HCID 86749182, compound

HRID 2260878Notes

Reaction equation

HRID 2260878 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:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)/[C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[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:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)\[C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 807IodineHCID 86749180HCID 86749180, compound

Product 1

HCID 86749182HCID 86749182, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Iodine (36 mg, 0.14 mmol) in CH2Cl2 (8 mL) was added over a period of 2 h at 0° C. to 7 (85 mg, 0.114 mmol) in CH2Cl2 (12 mL) under argon. Analysis by TLC (1:6CH2Cl2 :hexanes) indicated the disappearance of 7. The solution was warmed to room temperature, washed with NaHSO3 (2×20 mL) and KF (10 mL) solutions, dried (MgSO4), concentrated in vacuo, and the residue purified by flash column chromatography (1:4 CH2Cl2 :hexanes) to give 8 as a yellow solid (56.4 mg, 95% yield): 1H NMR δ 7.52 (d, J=10.5 Hz, 1 H), 7.2-7.4 (m, 10 H), 6.74 (d, J=10.5 Hz, 1 H), 4.11 (s, 2 H), 3.97 (s, 2 H), 0.27 (s, 9 H); 13C NMR δ 143.93, 136.42, 132.89, 129.20, 128.60, 127.62, 127.34, 120.75, 101.91, 95.48, 43.28, 37.36, -0.08; Anal., Calcd for C23H25IS2Si, C, 53.07; H, 4.84. Found C, 53.27; H, 5.00.

Workup

  1. washwashed with NaHSO3 (2×20 mL) and KF (10 mL) solutions
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash column chromatography (1:4 CH2Cl2 :hexanes)

Sources & evidence

ORD record
ord-17085acf697549488aad68718f1a11e1
Source dataset
uspto-grants-1995_12
Patent number
US05478959

Reaction notes

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