Sodium Bicarbonate → 3-Amino-1-(3-bromo-5-fluorophenyl)propan-1-ol

HRID 1484150Notes

Reaction equation

HRID 1484150 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:13])[CH2:10][C:11]#[N:12])[CH:5]=[C:6]([F:8])[CH:7]=1.CSC.B.C([O-])(O)=O.[Na+]>C1COCC1>[NH2:12][CH2:11][CH2:10][CH:9]([C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([Br:1])[CH:3]=1)[OH:13]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12423031(Dimethyl sulfide)trihydroboronHCID 689405323-(3-Bromo-5-fluorophenyl)-3-hydroxypropanenitrile

Product 1

HCID 651848593-Amino-1-(3-bromo-5-fluorophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-bromo-5-fluorophenyl)-3-hydroxypropanenitrile (2.50 g, 8.65 mmol) in THF (16.0 mL) was added borane methyl sulfide (1.20 g, 15.7 mmol). The mixture was heated to reflux for 2 h. After cooling to room temperature, saturated aqueous NaHCO3 (10 mL) was added and the mixture was stirred for 1 h. The THF was removed under reduced pressure and the remaining aqueous portion was extracted with ethyl acetate (2×60 ml). The extract was dried (Na2SO4) and concentrated to give 3-amino-1-(3-bromo-5-fluorophenyl)propan-1-ol that was used in following reaction without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. customThe THF was removed under reduced pressure
  4. extractionthe remaining aqueous portion was extracted with ethyl acetate (2×60 ml)
  5. dry with materialThe extract was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c80a241fd3aa4d8685f3858b6c4c3a19
Source dataset
uspto-grants-2016_08
Patent number
US09421210B2

Reaction notes

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