Iodine → HCID 19384259, compound

HRID 2399726Notes

Reaction equation

HRID 2399726 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([S:9][CH2:10][CH2:11][CH:12](F)[C:13](Br)([F:15])[F:14])[O:8][C:4]=2[CH:3]=1.CO.II.CCCCCC>C(OC(=O)C)C.[Zn].[I-].[Zn+2].[I-]>[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([S:9][CH2:10][CH2:11][CH:12]=[C:13]([F:15])[F:14])[O:8][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 807IodineHCID 887MethanolHCID 8058HexaneHCID 19384319HCID 19384319, compound

Product 1

HCID 19384259HCID 19384259, compoundYield 56.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 9883512zinc(II)iodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product of step 1 (5.27 g, 14.7 mmol), Methanol (50 cm3), zinc powder (9.66 g, 147 mmol), zinc iodide (catalytic), and iodine (catalytic) was refluxed for 18 hours. The reaction mixture was filtered and the filtrate partitioned between diethyl ether and 1.4M hydrochloric acid. The organic phase was washed with water, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure to give a brown oil. Chromatography on silica gel using 8:2 hexane:ethylacetate as eluent afforded the product as a white solid (2.13g). 1H NMR (CDCl3): δ7.45(1H,d); 6.95(1H,d); 6.8(1H,dd); 6.1(1H,s); 4.2-4.4(1H,m); 3.3(2H,t); 2.5(2H,m). M+ =257. m.p. 73.6°-75.4° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate partitioned between diethyl ether and 1.4M hydrochloric acid
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a brown oil

Sources & evidence

ORD record
ord-8b2236e5e78e44978cbd07300ff1b48c
Source dataset
uspto-grants-1995_09
Patent number
US05451594

Reaction notes

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