Sodium Hydroxide → HCID 66879256, compound

HRID 39006Notes

Reaction equation

HRID 39006 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]([F:12])[C:6]=1[O:13][CH2:14][C@H:15]1[CH2:17][O:16]1)(=O)C.[OH-].[Na+]>O1CCOCC1>[Br:11][C:9]1[CH:8]=[C:7]([F:12])[C:6]2[O:13][CH2:14][C@H:15]([CH2:17][OH:16])[O:4][C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866529465-Bromo-3-fluoro-2-[(2R)-oxiran-2-ylmethoxy]phenyl acetate

Product 1

HCID 66879256HCID 66879256, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-(5-bromo-3-fluoro-2-[(2R)-oxiran-2-ylmethoxy]phenyl acetate (crude, max 67 mmol) was stirred in dioxane at 0° C. NaOH (15%) was added until the mixture reached pH 14. The mixture was stirred for 30 min at RT and then concentrated. Water was added and the mixture extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness to give the crude title compound. Yield: 10.3 g. MS m/z (rel. intensity, 70 eV) 262 (M+, bp), 264 (M+, bp), 206 (70), 81 (58), 69 (55), 57 (53).

Workup

  1. concentrationconcentrated
  2. additionWater was added
  3. extractionthe mixture extracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-32a2f494200a4a5bbc14c29820a1e1b8
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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