Bromine → HCID 54543492, compound

HRID 1378563Notes

Reaction equation

HRID 1378563 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=1.[Br:19]Br>C(O)(=O)C.Br>[Br:19][CH:9]([C:10]1[CH:11]=[CH:12][C:13]([S:16][CH3:17])=[CH:14][CH:15]=1)[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:18]

Participants

5

Reactant 2

HCID 24408BromineHCID 53715534HCID 53715534, compound

Product 1

HCID 54543492HCID 54543492, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 260Hydrogen BromideSolvent

Procedure

A solution of the ketone from Step 2 (5.92 g, 23.1 mmol) in acetic acid (50 mL) and 33% HBr in acetic acid (2 mL) was treated with a 1.1M solution of bromine in acetic acid (21.7 mL, 23.8 mmol) and stirred at room temperature for 2 hours. The solution was concentrated in vacuo and the residue taken up in dichloromethane, washed with 1N NaHSO3 and sat. aq. NaHCO3, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give a yellow solid which was used directly in the next step without further purification (5.97 g, 77%): mp 85°-89° C. 1H NMR (CDCl3) 300 MHz 7.56 (d, J=7.9 Hz, 1H), 7.41 (d, J=8.5 Hz, 2H), 7.37 (d, J=7.7 Hz, 1H), 7.22 (m, 4H), 6.18 (s, 1H), 2.47 (s, 3H), 2.44 (s, 3H). Mass spectrum M+H=341.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washwashed with 1N NaHSO3 and sat. aq. NaHCO3
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a yellow solid which
  7. customwas used directly in the next step without further purification (5.97 g, 77%)

Sources & evidence

ORD record
ord-2bd92b9639e94f7b8b15c66a87ef7251
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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