HCID 21999531, compound → HCID 21999543, compound

HRID 1275939Notes

Reaction equation

HRID 1275939 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, 1 F); 141.69 (dd, J=10.0, 20.1 Hz, 1 F); 143.05 (dt, J=5.8, 23.1 Hz, 1 F); 155.48 (dd, J=10.2, 22.8 Hz, 1 F); 155.67 (s, 1 F); 156.27 (dd, J=5.8, 20.5 Hz, 1 F); 158.57 (t, J=22.2 Hz, 1 F); 162.5 (b, 1 F).

Workup

  1. temperatureat reflux
  2. customis purified by column chromatography

Sources & evidence

ORD record
ord-12137f89bd3d4b178a849dc8812bb283
Source dataset
uspto-grants-2000_12
Patent number
US06162931

Reaction notes

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