Trifluoroacetic acid → HCID 58488401, compound

HRID 2194871Notes

Reaction equation

HRID 2194871 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[O-:11][C:12]#[N:13].[Na+].C(O)(C(F)(F)F)=O>C1C=CC=CC=1.[OH-].[Na+]>[C:12](=[O:11])([O:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[NH2:13]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 517096Sodium CyanateHCID 27340892-(2-Bromophenyl)ethan-1-ol

Product 1

HCID 58488401HCID 58488401, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of commercially available 2-(2-bromophenyl)ethanol (1 eq.) in Benzene (0.85M) at room temperature was added sodium cyanate (2.1 eq) then TFA (2.2 eq) dropwise. The mixture was stirred at room temperature for 6 h, poured in aqueous NaOH (1N) and extracted with EtOAc. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated. Recrystallization in Et2O afforded the desired compound as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customRecrystallization in Et2O

Sources & evidence

ORD record
ord-a9f1ca8dd42a45dcb3f80a3163ff97e0
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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