Triethylamine → HCID 67294198, compound

HRID 518007Notes

Reaction equation

HRID 518007 reaction equation
[H-].[Na+].C(N(CC)CC)C.[OH:10][CH2:11][CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[Br:22][C:23]1[CH:28]=[CH:27][C:26](F)=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=1>CN(C=O)C.CCOC(C)=O>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([O:10][CH2:11][CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[C:25]([C:30]([F:31])([F:32])[F:33])[CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 27363255-Bromo-2-fluorobenzotrifluoride

Product 1

HCID 67294198HCID 67294198, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (247 mmol, 9.88 g) was stirred in DMF (100 ml) at room temperature. triethylamine (165 mmol, 22.88 ml, 16.66 g) was added. tert-butyl 2-hydroxyethyl(methyl)carbamate (173 mmol, 30.3 g) was added dropwise in DMF. 4-bromo-1-fluoro-2-(trifluoromethyl)benzene (165 mmol, 40 g) was added in one portion and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and washed with water. The organic was dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by flash chromatography eluting with heptane—60/40 heptane/EtOAc. Fractions were collected and combined to afford tert-butyl 2-(4-bromo-2-(trifluoromethyl)phenoxy)-ethyl(methyl)carbamate. (18.44 g)

Workup

  1. washwashed with water
  2. dry with materialThe organic was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by flash chromatography
  5. washeluting with heptane—60/40 heptane/EtOAc
  6. customFractions were collected

Sources & evidence

ORD record
ord-a89bf70a85c048238276ad8e8446694a
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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