Sodium Sulfite → HCID 118022035, compound

HRID 575825Notes

Reaction equation

HRID 575825 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]SCC)[CH:5]=[CH:4][C:3]=1[O:12][CH2:13][C:14]([F:17])([F:16])[F:15].[CH:18]1C=C(Cl)C=C(C(OO)=O)[CH:19]=1.[O-:29][S:30]([O-:32])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][S:30]([CH2:18][CH3:19])(=[O:32])=[O:29])[CH:5]=[CH:4][C:3]=1[O:12][CH2:13][C:14]([F:15])([F:17])[F:16]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 118022789HCID 118022789, compound

Product 1

HCID 118022035HCID 118022035, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of the title compound from Step 4 (2.10 g, 6.38 mmol) in DCM (210 mL) was added MCPBA (4.41 g, 25.53 mmol) in several portions. The mixture was stirred at 25° C. for 12 hrs. The reaction was poured into sat. aq. Na2SO3 (100 mL) and extracted with DCM (80 mL×3). The combined organic layers were washed with sat. NaHCO3 (100 mL×2) and brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE:EA=1:02:1) to give the title compound (2.10 g, 91%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.64 (d, J=2.0 Hz, 1H), 7.37 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 4.43 (q, J=8.0 Hz, 2H), 4.15 (s, 2H), 2.91 (q, J=7.6 Hz, 2H), 1.39 (t, J=7.6 Hz, 3H).

Workup

  1. extractionextracted with DCM (80 mL×3)
  2. washThe combined organic layers were washed with sat. NaHCO3 (100 mL×2) and brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (PE:EA=1:02:1)

Sources & evidence

ORD record
ord-25f6261def6d4153bb2f56c24a06076d
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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