2-Bromoethanol → HCID 22458112, compound

HRID 2184840Notes

Reaction equation

HRID 2184840 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].Br[CH2:14][CH2:15][OH:16]>C(Cl)Cl>[OH:16][CH2:15][CH2:14][NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[O:3][C:2]([F:11])([F:12])[F:1]

Participants

4

Reactant 2

HCID 108982-BromoethanolHCID 737542-(Trifluoromethoxy)aniline

Product 1

HCID 22458112HCID 22458112, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
115 °C

Procedure

A stirred mixture of 5.64 g of 97% 2-trifluoromethoxyaniline and 3.4 mL of 97% 2-bromoethanol was heated at 115° C. for 8 h. After cooling to r.t., 50 ml, of CH2Cl2 was added and the solution was washed with 20% aq. sodium carbonate and H2O (3×20 mL), dried (anhydrous Na2SO4) and evaporated to dryness in vacuo. The residue was purified by flash chromatography (CHCl3-2 N methanolic NH3 100:0.5) affording 3.18 g (46.5%) of the title compound as a yellow oil.

Workup

  1. temperatureAfter cooling to r.t.
  2. washthe solution was washed with 20% aq. sodium carbonate and H2O (3×20 mL)
  3. dry with materialdried (anhydrous Na2SO4)
  4. customevaporated to dryness in vacuo
  5. customThe residue was purified by flash chromatography (CHCl3-2 N methanolic NH3 100:0.5)

Sources & evidence

ORD record
ord-7361175f1c1345fd8a795fb4d8054810
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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