Bromine → HCID 22398537, compound

HRID 2080606Notes

Reaction equation

HRID 2080606 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=[O:17])[CH2:4][C:5]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].[Br:20]Br>C(O)(=O)C>[Br:20][C:12]1[C:11]([F:14])=[CH:10][C:9]([O:15][CH3:16])=[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4][C:3](=[O:17])[C:2]([F:1])([F:18])[F:19])[CH:13]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 22398549HCID 22398549, compound

Product 1

HCID 22398537HCID 22398537, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 300 mg (1.078 mmol) of 1,1,1-trifluoro-4-(4-fluoro-2-methoxyphenyl)-4-methylpentan-2-one (Example 26) in 0.5 mL of acetic acid was added 70 μL (1.35 mmol) of bromine. The reaction was monitored by TLC (EtOAc-hexanes (1:9)) by partitioning an aliquot between saturated aqueous sodium bicarbonate and EtOAc. A new slightly more polar product was observed. The reaction was made basic with saturated aqueous sodium bicarbonate and extracted with three 15 mL portion of EtOAc. The combined organic layers were washed with two 10 mL portions of saturated aqueous sodium bicarbonate and 10 mL of brine, dried over magnesium sulfate, filtered, and concentrated. The residue was dissolved in hexanes and passed through a pad of silica gel, eluting with EtOAc-hexanes (0.5:99.5) to afford 375 mg (97%) of the title compound.

Workup

  1. customby partitioning an aliquot between saturated aqueous sodium bicarbonate and EtOAc
  2. extractionextracted with three 15 mL portion of EtOAc
  3. washThe combined organic layers were washed with two 10 mL portions of saturated aqueous sodium bicarbonate and 10 mL of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in hexanes
  8. washeluting with EtOAc-hexanes (0.5:99.5)

Sources & evidence

ORD record
ord-c84a99e1b81f415ab1c00461fae3b455
Source dataset
uspto-grants-2011_04
Patent number
US07932392B2

Reaction notes

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