Water → HCID 57531205, compound

HRID 1454918Notes

Reaction equation

HRID 1454918 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[C:4]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:3]=1.[OH2:18]>C(OCC)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]2[C:6](=[O:18])[C:16]3[C:11]([S:10][C:4]=2[CH:3]=1)=[CH:12][C:13]([F:17])=[CH:14][CH:15]=3

Participants

4

Reactant 2

HCID 962WaterHCID 69074519HCID 69074519, compound

Product 1

HCID 57531205HCID 57531205, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

Mix 4-fluoro-2-(3-fluoro-phenylsulfanyl)-benzonitrile (15.7 g, 63 mmol) and polyphosphoric acid (60 g), heat to 200° C. for 10 days. Dilute with H2O (300 mL) and ethyl acetate (700 mL), and filter through a pad of celite. Separate layers formed in the filtrate, and extract aqueous with two 150 mL portions of ethyl acetate. Combine organics, dry (MgSO4), filter, and concentrate to a brown solid. Purify on silica gel (0-10% ethyl acetae/hexanes)to afford 430 mg (3%) of the title compound as a yellow solid. MS [EI] 248; HPLC shows 92% purity; 1H-NMR consistent with structure. 1H-NMR (CDCl3) δ 8.67 (dd, 2H, J=9.0, 5.9 Hz), 7.26 (m, 4H).

Workup

  1. filtrationfilter through a pad of celite
  2. customSeparate layers formed in the filtrate
  3. extractionextract aqueous with two 150 mL portions of ethyl acetate
  4. dry with materialCombine organics, dry (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate to a brown solid
  7. customPurify on silica gel (0-10% ethyl acetae/hexanes)

Sources & evidence

ORD record
ord-faf746f9c27f437299ac92a7922caf81
Source dataset
uspto-grants-2009_01
Patent number
US07482344B2

Reaction notes

Loading…