Trimethylphosphine → 1-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamine

HRID 511002Notes

Reaction equation

HRID 511002 reaction equation
[N:1]([CH:4]([C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([F:13])=[C:8]([Br:14])[C:7]=1[O:15][CH3:16])[CH3:5])=[N+]=[N-].CP(C)C>C1COCC1.O.CCOC(C)=O>[Br:14][C:8]1[C:7]([O:15][CH3:16])=[C:6]([CH:4]([NH2:1])[CH3:5])[CH:11]=[C:10]([Cl:12])[C:9]=1[F:13]

Participants

6

Reactant 2

HCID 68983TrimethylphosphineHCID 866669151-(1-Azidoethyl)-3-bromo-5-chloro-4-fluoro-2-methoxybenzene

Product 1

HCID 866669161-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamineYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To the stirred solution of 1-(1-azidoethyl)-3-bromo-5-chloro-4-fluoro-2-methoxybenzene (3.3 g, 11 mmol) in THF (50 mL) and water (10 mL) was added 1.0 M trimethylphosphine in THF (13 mL) at room temperature and the mixture was stirred for 1 hour. The mixture was diluted with EtOAc, washed with saturated sodium bicarbonate solution, water, brine, dried over magnesium sulfate and concentrated to give the desired compound (2.9 g, 95%). LCMS calculated for C9H8BrClFO (M−NH2)+: m/z=264.9, 266.9. found: 265.0, 267.0.

Workup

  1. washwashed with saturated sodium bicarbonate solution, water, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7eb24891433d49f39b0ec016251f870c
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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