HCID 86650269, compound → 2-Amino-2-(5-bromo-2-fluoro-phenyl)-propane-1,3-diol

HRID 81587Notes

Reaction equation

HRID 81587 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]([N+:13]([O-])=O)([CH2:11][OH:12])[CH2:9][OH:10])[CH:7]=1>CC(O)=O.[Zn]>[NH2:13][C:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:16])([CH2:9][OH:10])[CH2:11][OH:12]

Participants

4

Reactant 1

HCID 86650269HCID 86650269, compound

Product 1

HCID 666658452-Amino-2-(5-bromo-2-fluoro-phenyl)-propane-1,3-diol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

A solution of 2-(5-bromo-2-fluoro-phenyl)-2-nitro-propane-1,3-diol (7 g, 23.8 mmol) in 35 ml AcOH was added dropwise to a mixture of zinc (9.34 g, 143 mmol) in 35 ml AcOH while the temperature did not rise above 40° C. The mixture was stirred for 1 h, filtered over celite and washed with MeOH. The filtrate was evaporated, diluted with water and washed with TBME. The aqueous layer was basified with 2 N NaOH and NH3 (25%, aqueous), saturated with NaCl and extracted with EtOAc. The organic layer was washed with brine, dried with Na2SO4 and evaporated to provide the title compound as an off-white solid.

Workup

  1. customdid not rise above 40° C
  2. filtrationfiltered over celite
  3. washwashed with MeOH
  4. customThe filtrate was evaporated
  5. additiondiluted with water
  6. washwashed with TBME
  7. extractionextracted with EtOAc
  8. washThe organic layer was washed with brine
  9. dry with materialdried with Na2SO4
  10. customevaporated

Sources & evidence

ORD record
ord-05ab8ee0184f4cc2a47e88943afdb34f
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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