Sodium Chloride → HCID 90413332, compound

HRID 1746049Notes

Reaction equation

HRID 1746049 reaction equation
[F:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[C:4]([F:11])[CH:3]=1.[I:12]N1C(=O)CCC1=O.FC(F)(F)C(O)=O.OS([O-])=O.[Na+].[Na+].[Cl-]>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[C:4]([F:11])[C:3]=1[I:12]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 23665763Sodium BisulfiteHCID 90413773HCID 90413773, compound

Product 1

HCID 90413332HCID 90413332, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4,6-Difluorobenzo[d][1,3]dioxole (300 mg, 1.9 mmol) and N-iodosuccinimide (640 mg, 2.9 mmol) were combined in dry acetonitrile (5 mL), treated with trifluoroacetic acid (430 mg, 3.8 mmol) and stirred for 20 h. The mixture was stirred with a solution of NaHSO3 (100 mg in 2 mL water) and then shaken with ethyl acetate (30 mL) and saturated NaCl (5 mL). The organic phase was washed with saturated NaCl (5 mL), dried (Na2SO4) and evaporated. The material was purified by chromatography on silica with a 0-5% ethyl acetate-hexane gradient to give the title compound as a white solid (410 mg, 76%): mp 65-66° C. 1H NMR (400 MHz, CDCl3) δ 6.54 (dd, J=6.9, 1.6 Hz, 1H), 6.07 (s, 2H); 19F NMR (376 MHz, CDCl3) δ −99.31, −117.98; EIMS m/z 284.

Workup

  1. washThe organic phase was washed with saturated NaCl (5 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe material was purified by chromatography on silica with a 0-5% ethyl acetate-hexane gradient

Sources & evidence

ORD record
ord-d9e5582d2d244c1da1aab3f9e88cd4f1
Source dataset
uspto-grants-2015_10
Patent number
US09149038B2

Reaction notes

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