Water → HCID 66820102, compound

HRID 1044789Notes

Reaction equation

HRID 1044789 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([F:12])[C:6]=1[F:13])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][NH2:1])=[C:6]([F:13])[C:7]=1[F:12]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 91256229Benzene, 1-(azidomethyl)-4-bromo-2,3-difluoro-

Product 1

HCID 66820102HCID 66820102, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of the crude azide (164 mg, 0.60 mmol) in THF (3 mL) were added polymer-supported Ph3P (2.0 eq.) and water (1 mL). The reaction mixture was stirred at 55° C. until completion of the reaction, cooled down to rt and filtered. The filtrate was partitioned between EA and aq. sat. NaHCO3 and the layers separated. The aq. layer was extracted with EA and the combined org. extracts dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 07: tR=0.42 min; [M+CH3CN+H]+=263.15.

Workup

  1. temperaturecooled down to rt
  2. filtrationfiltered
  3. customThe filtrate was partitioned between EA and aq. sat. NaHCO3
  4. customthe layers separated
  5. extractionThe aq. layer was extracted with EA
  6. dry with materialextracts dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c9d4931848d466ca076fad9b4a3ab7c
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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