Trimethylphosphine → HCID 86711472, compound

HRID 2274122Notes

Reaction equation

HRID 2274122 reaction equation
[N:1]([CH:4]([C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([Cl:13])=[C:8]([I:14])[C:7]=1[O:15][CH3:16])[CH3:5])=[N+]=[N-].CP(C)C>O1CCCC1.O>[Cl:13][C:9]1[C:10]([Cl:12])=[CH:11][C:6]([CH:4]([NH2:1])[CH3:5])=[C:7]([O:15][CH3:16])[C:8]=1[I:14]

Participants

5

Reactant 2

HCID 68983TrimethylphosphineHCID 86711473HCID 86711473, compound

Product 1

HCID 86711472HCID 86711472, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 1-(1-azidoethyl)-4,5-dichloro-3-iodo-2-methoxybenzene (3.3 g, 8.9 mmol) in tetrahydrofuran (20 mL) and water (6.4 mL) was treated with 1.0 M trimethylphosphine in tetrahydrofuran (11 mL, 11 mmol) and stirred at 20° C. for 1.5 hours. The reaction mixture was concentrated, diluted with ethyl acetate and extracted with 1 M HCl (2×). The combined aqueous layers were neutralized with solid sodium bicarbonate, and extracted with ethyl acetate (2×). The combined organic extracts were washed with brine, dried with magnesium sulfate, filtered, and concentrated to give the desired product (2.2 g, 72%). This material was used without further purification. LCMS for C9H8Cl2IO (M−NH2)+: m/z=328.9, 330.9. Found: 328.8, 330.8.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. extractionextracted with 1 M HCl (2×)
  4. extractionextracted with ethyl acetate (2×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4a0f6510401f45c4b2561a8f7f59b5bf
Source dataset
uspto-grants-2015_09
Patent number
US09126948B2

Reaction notes

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