Sodium hydride → HCID 67333125, compound

HRID 2102217Notes

Reaction equation

HRID 2102217 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1)=[O:3].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](OC)=[O:24])=[CH:18][CH:17]=1.[H-].[Na+]>C1COCC1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=[O:24])[CH2:1][C:2]([C:4]2[CH:5]=[CH:6][C:7]([O:10][C:11]([F:12])([F:13])[F:14])=[CH:8][CH:9]=2)=[O:3])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 5228211-(4-(Trifluoromethoxy)phenyl)ethan-1-one

Product 1

HCID 67333125HCID 67333125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.40 g 4-trifluoromethoxyacetophenone and 7.57 g methyl 4-bromophenylacetate in 60 mL anhydrous THF was treated with 1.59 g 60% NaH for 60 hours. After removing the solvent under reduced pressure, the reaction mixture was diluted with 250 mL ether and washed with 250 mL 0.2 M HCl, 2×100 mL 5% NaHCO3 and 100 mL saturated brine, dried over anhydrous Na2SO4, and evaporated to give a crude product. It was purified on silica gel using 0-25% EtOAc in hexanes to give title compound as red oil. 1H NMR (CDCl3, 500 MHz) δ 7.86˜7.89 (m, 2H), 7.48˜7.51 (m, 2H), 7.27 (d, J=7 Hz, 2H), 7.17˜7.19 (m, 2H), 6.07 (s, 1H), 3.70 (s, 2H).

Workup

  1. customAfter removing the solvent under reduced pressure
  2. additionthe reaction mixture was diluted with 250 mL ether
  3. washwashed with 250 mL 0.2 M HCl, 2×100 mL 5% NaHCO3 and 100 mL saturated brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated
  6. customto give a crude product
  7. customIt was purified on silica gel using 0-25% EtOAc in hexanes

Sources & evidence

ORD record
ord-87359977c00448cf82b387ead000d993
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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