Trifluoroacetic acid → HCID 67514531, compound

HRID 1519551Notes

Reaction equation

HRID 1519551 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[I:12]N1C(=O)CCC1=O.C(O)(C(F)(F)F)=O>>[F:1][C:2]1[C:9]([I:12])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 27833294-Fluoro-2-methoxybenzonitrile

Product 1

HCID 67514531HCID 67514531, compound

Procedure

To 4-fluoro-2-methoxybenzonitrile (3.00 g, 20 mmol) and N-iodosuccinimide (NIS) (4.7 g, 21 mmol) under nitrogen was added TFA (35 mL) and the reaction was stirred at room temperature for 20 hours. The volatiles were removed in vacuo and the residue was taken up in 1:1 ethyl acetate:ether and was washed with aqueous sodium bicarbonate and then brine containing enough sodium sulfite to remove the iodine color. The aqueous layers were back extracted with more 1:1 ethyl acetate:ether and the combined organic layers were dried over sodium sulfate and evaporated. The residue was treated with ether/hexanes to afford clean iodo title product as a white solid. 1H-NMR (500 MHz, CDCl3) δ ppm 3.930 (s, 3H), 6.730 (d, J=9.4 Hz, 1H), 7.900 (d, J=6.8 Hz, 1H).

Workup

  1. customThe volatiles were removed in vacuo
  2. washether and was washed with aqueous sodium bicarbonate
  3. custombrine containing enough sodium sulfite to remove the iodine color
  4. extractionThe aqueous layers were back extracted with more 1:1 ethyl acetate
  5. dry with materialether and the combined organic layers were dried over sodium sulfate
  6. customevaporated
  7. additionThe residue was treated with ether/hexanes

Sources & evidence

ORD record
ord-d80268877fac4712bda59d5ea6499aa9
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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