Triphenylphosphine → 2-(4-Bromo-2-(trifluoromethyl)phenoxy)ethanamine

HRID 518003Notes

Reaction equation

HRID 518003 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][NH2:1])=[C:8]([C:14]([F:15])([F:16])[F:17])[CH:9]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 866733571-(2-Azidoethoxy)-4-bromo-2-(trifluoromethyl)benzene

Product 1

HCID 654849992-(4-Bromo-2-(trifluoromethyl)phenoxy)ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Azidoethoxy)-4-bromo-2-(trifluoromethyl)benzene (7.32 mmol, 2.271 g) and triphenylphosphine (10.99 mmol, 2.88 g) were combined and stirred for 1 hour in THF (5 ml). The reaction mixture was concentrated in vacuo. The residue was taken up in EtOAc/water, the layers separated and the organic dried over sodium sulfate and concentrated in vacuo. The resulting residue was passed down an SCX column to afford 2-(4-bromo-2-(trifluoromethyl)phenoxy)ethanamine. (1.30 g)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe layers separated
  3. dry with materialthe organic dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e492757b00f436a87824489d860d3f6
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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