Iodine → HCID 12764464, compound

HRID 1387197Notes

Reaction equation

HRID 1387197 reaction equation
FC(F)(F)C(O[IH][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[IH:13]OC(=O)C(F)(F)F)=O.[C:23]1([C:29]23[CH2:38][CH:33]4[CH2:34][CH:35]([CH2:37][C:31](C5C=CC=CC=5)([CH2:32]4)[CH2:30]2)[CH2:36]3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[I:45]I>C(Cl)Cl>[I:45][C:26]1[CH:27]=[CH:28][C:23]([C:29]23[CH2:38][CH:33]4[CH2:34][CH:35]([CH2:37][C:31]([C:11]5[CH:12]=[CH:7][C:8]([I:13])=[CH:9][CH:10]=5)([CH2:32]4)[CH2:30]2)[CH2:36]3)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 807IodineHCID 38714511,3-diphenyladamantaneHCID 178526051HCID 178526051, compound

Product 1

HCID 12764464HCID 12764464, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis((trifluoroacetoxy)iodo)benzene (26.24 g, 0.061 mol) and 1,3-diphenyl adamantane (16.00 g, 0.055 mol) and were dissolved in 150 mL of anhydrous CH2Cl2. To this solution was added sublimed iodine (14.08 g, 0.055 mol) and the dark purple solution was stirred at room temperature under dry nitrogen for 3 h until the pink color disappeared. Most of the product precipitated out of reaction as white fine crystals. The crystals were collected by filtration and washed with minimum amount of CH2Cl2 to give 24.0 g of pure product. The filtrate was washed with dilute sodium thiosulfate solution (2×80 mL), water (1×80 mL), and dried over MgSO4. Solvent was evaporated and the residue was washed with acetone and filtered to give 2.90 g product (total yield 90%). 1H NMR (CDCl3) δ (ppm): 1.76 (s, 2H), 1.88 (s, 8H), 1.93 (s, 2H), 2.30 (s, 2H), 7.10 (d, J=8.5 Hz, 4H, aromatic), 7.6 (d, J=8.5 Hz, 4H, aromatic); 13C NMR (CDCl3): 29.33, 35.61, 37.14, 41.96, 48.52, 91.04, 127.11, 137.21, 150.05. M.p. 100-102° C.; FD-MS: m/z 540 (M+).

Workup

  1. customMost of the product precipitated out of reaction as white fine crystals
  2. filtrationThe crystals were collected by filtration
  3. washwashed with minimum amount of CH2Cl2

Sources & evidence

ORD record
ord-10fbd8d0fe9449739a604b2b59d0e65f
Source dataset
uspto-grants-2001_07
Patent number
US06268072B1

Reaction notes

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