Iodine → HCID 67287426, compound

HRID 1191975Notes

Reaction equation

HRID 1191975 reaction equation
[N+:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:12])([O-:3])=[O:2].C(=O)(O)[O-].[Na+].[I:18]I>>[I:18][C:6]1[C:5]([OH:12])=[C:4]([N+:1]([O-:3])=[O:2])[C:9]([O:10][CH3:11])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 15654643HCID 15654643, compound

Product 1

HCID 67287426HCID 67287426, compoundYield 96%

Conditions

Temperature
0 °C

Procedure

A mixture of 1.36 g (8 mmol) of the product of Step 1 and 0.68 g (8 mmol) of sodium bicarbonate was sonicated at room temperature until it become homogenous. The resulting mixture was cooled to 0° C. and 2.04 g (8 mmol) of iodine was added. After stirring for 1 h at room temperature the precipitate formed was filtered off, dried and recrystallized from ethyl ether to give 2.28 g (96% yield of pure title compound as an orange crystals; 1H NMR (CDCl3) 3.92 (s, 3H, OMe); 6.41 (d, 1H, CH J=9 Hz); 7.82 (d, 1H, J=9 Hz); 10.37 (s, 1H, OH).

Workup

  1. customwas sonicated at room temperature until it
  2. customformed
  3. filtrationwas filtered off
  4. customdried
  5. customrecrystallized from ethyl ether

Sources & evidence

ORD record
ord-e24308b3596d449ca2afbaad4cdb00e8
Source dataset
uspto-grants-2014_03
Patent number
US08680135B2

Reaction notes

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