Iodine → HCID 90413589, compound

HRID 1746047Notes

Reaction equation

HRID 1746047 reaction equation
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[C:8]([F:12])[CH:9]=[C:10]([F:11])[C:4]=2[O:3]1.[Li]C(CC)C.[I:19]I.[NH4+].[Cl-]>O1CCCC1>[F:13][C:2]1([F:1])[O:6][C:5]2[CH:7]=[C:8]([F:12])[C:9]([I:19])=[C:10]([F:11])[C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 90415324HCID 90415324, compoundHCID 178418400CID 53628100

Product 1

HCID 90413589HCID 90413589, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

2,2,4,6-Tetrafluorobenzo[d][1,3]dioxole (500 mg, 2.6 mmol) was dissolved in dry tetrahydrofuran (7 mL), cooled to −70° C., treated dropwise with sec-BuLi (1.3 M; 2.1 mL, 2.7 mmol) and stirred for 1 h at −70° C. This mixture was treated dropwise with a solution of iodine (1.1 g, 4.4 mmol) in tetrahydrofuran (5 mL) over 10 min. After 2 h at −70° C., the mixture was treated with saturated NH4Cl, extracted with ethyl ether, dried (Na2SO4) and evaporated. The material was purified by reverse phase HPLC with 85% acetonitrile-water to give the title compound (250 mg; 30%): 1H NMR (400 MHz, CDCl3) δ 6.80-6.77 (d, J=8.7 Hz, 1H), 6.77-6.75 (d, J=8.7 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −48.72, −99.73, −132.62; EIMS m/z 320.

Workup

  1. waitAfter 2 h at −70° C.
  2. extractionextracted with ethyl ether
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe material was purified by reverse phase HPLC with 85% acetonitrile-water

Sources & evidence

ORD record
ord-34650789ee5240d890681197cb1929cd
Source dataset
uspto-grants-2015_10
Patent number
US09149038B2

Reaction notes

Loading…