Triphenylphosphine → HCID 71270516, compound

HRID 2409480Notes

Reaction equation

HRID 2409480 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C@@H:10]([N:12]=[N+]=[N-])[CH3:11].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C@@H:10]([NH2:12])[CH3:11]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 70970331HCID 70970331, compound

Product 1

HCID 71270516HCID 71270516, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S)-2-(2-bromo-5-fluorophenyl)-1-methylethyl azide (1.00 g, 3.87 mmol) in 20 mL of THF and 4 mL of water was added PPh3 (2.03 g, 7.74 mmol) and the mixture was stirred for 4 h. The solvent was evaporated and the residue was purified by silica gel column eluting first with DCM, then DCM:MeOH:NH4OH (94:5:1). The fraction with product was evaporated to give (1S)-2-(2-bromo-5-fluorophenyl)-1-methylethylamine (134 mg, 15%) as colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.50 (m, 1H), 6.97 (m, 1H), 6.83 (m, 1H), 3.28 (m, 1H), 2.66-2.87 (m, 2H), 1.68 (s, 2H), 1.17 (d, J=6.21 Hz, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column
  3. washeluting first with DCM
  4. customThe fraction with product was evaporated

Sources & evidence

ORD record
ord-618d89c3ef1d43c9b9b9209c488c6253
Source dataset
uspto-grants-2014_08
Patent number
US08815906B2

Reaction notes

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