Sodium hydride → HCID 89648734, compound

HRID 1773964Notes

Reaction equation

HRID 1773964 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([Br:15])[CH:9]=1)[CH3:4].FC(F)(F)S(O[CH2:23][CH:24]([F:26])[F:25])(=O)=O>C1COCC1>[CH2:3]([O:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:23][CH:24]([F:26])[F:25])=[C:10]([Br:15])[CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 18620106Ethyl 2-(3-bromo-4-hydroxyphenyl)acetate

Product 1

HCID 89648734HCID 89648734, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride 60% dispersion in mineral oil (80 mg, 2.0 mmol, 1.0 eq.) was added portionwise to an ice-cooled solution of (3-bromo-4-hydroxy-phenyl)-acetic acid ethyl ester (564 mg, 2.0 mmol, 1.0 eq.) in THF (9.4 mL). The ice bath was removed and the mixture was allowed to warm to r.t. and stirred for 30 min. A solution of 2,2-difluoroethyl trifluoromethanesulfonate (961 mg, 4.4 mmol, 2.2 eq.) in THF (1 mL) was added and the resulting mixture was stirred at r.t. for 18 hours. The mixture was concentrated in vacuo. The residue was taken up in DCM and water was added. The layers were separated and the aq. phase was extracted with DCM (3×). The comb. org. layers were washed with sat. aq. NaCl soln., dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a yellow oil. The product was used without further purification.

Workup

  1. customThe ice bath was removed
  2. stirringthe resulting mixture was stirred at r.t. for 18 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. additionwater was added
  5. customThe layers were separated
  6. extractionthe aq. phase was extracted with DCM (3×)
  7. washlayers were washed with sat. aq. NaCl soln
  8. dry with material, dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-045f43304194476a8bc6f4c41ff807b5
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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