Bromine → HCID 53933001, compound

HRID 1378559Notes

Reaction equation

HRID 1378559 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1.[Br:20]Br>C(O)(=O)C.Br>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[CH:10]([Br:20])[C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 23372840HCID 23372840, compound

Product 1

HCID 53933001HCID 53933001, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 260Hydrogen BromideSolvent

Procedure

A solution of the ketone intermediate from Step 2 (2.05 g, 7.4 mmol) in acetic acid (30 mL) and 33% HBr in acetic acid (0.5 mL) was treated with a 0.99M solution of bromine in acetic acid (7.6 mL, 7.5 mmol) and stirred at room temperature for 1 hour. The solution was concentrated in vacuo and the residue was taken up in dichloromethane, washed with 1N NaHSO3, brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give a brown solid (2.39 g, 90%) that was unstable and used directly in the next step without further purification. 1H NMR (CDCl3) 300 MHz 7.94 (q, J=6.3 Hz, 1H), 7.37 (d, J=8.5 Hz, 2H), 7.21 (d, J=8.5 Hz, 2H), 6.97 (m, 1H), 6.84 (m, 1H), 6.28 (s, 1H), 2.46 (s, 3H); 19F NMR (CDCl3) -100.31 (m), -103.50 (m). Mass spectrum: M+H=358.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washwashed with 1N NaHSO3, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-310e60abf6ac4a95a82a864de4a6961a
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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