HCID 21999531, compound → HCID 21999543, compound

HRID 1976940Notes

Reaction equation

HRID 1976940 reaction equation
C[O:2][C:3]1[C:21]([F:22])=[C:20]([O:23]C)[C:19]([F:25])=[C:18]([F:26])[C:4]=1[C:5]([C:7]1[C:12]([F:13])=[C:11]([F:14])[C:10]([F:15])=[C:9]([F:16])[C:8]=1[F:17])=[O:6]>C(O)(=O)C.Br>[OH:2][C:3]1[C:21]([F:22])=[C:20]([OH:23])[C:19]([F:25])=[C:18]([F:26])[C:4]=1[C:5]([C:7]1[C:12]([F:13])=[C:11]([F:14])[C:10]([F:15])=[C:9]([F:16])[C:8]=1[F:17])=[O:6]

Participants

4

Reactant 1

HCID 21999531HCID 21999531, compound

Product 1

HCID 21999543HCID 21999543, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of Compound 45 (450 mg, 1.17 mmol) in 5 mL acetic acid and 5 mL 48% hydrobromic acid is heated for 48 hours at reflux. The reaction mixture is worked up as above, and the crude product is purified by column chromatography to yield 362 mg (87%) of Compound 46 as a colorless solid. 19F NMR (d6-DMSO) 139.80 (m, 1F); 141.69 (dd, J=10.0, 20.1 Hz, 1F); 143.05 (dt, J=5.8, 23.1 Hz, 1F); 155.48 (dd, J=10.2, 22.8 Hz, 1F); 155.67 (s, 1F); 156.27 (dd, J=5.8, 20.5 Hz, 1F); 158.57 (t, J=22.2 Hz, 1F); 162.5 (b, 1F).

Workup

  1. temperatureat reflux
  2. customis purified by column chromatography

Sources & evidence

ORD record
ord-9b8527867a1a4b7d8ab122828b72226b
Source dataset
uspto-grants-2001_05
Patent number
US06229055B1

Reaction notes

Loading…