Triphenylphosphine → HCID 15678619, compound

HRID 1460340Notes

Reaction equation

HRID 1460340 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)[CH2:10]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:43]N1C(=O)CCC1=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)[CH2:10][Br:43])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 67184N-bromobutanimideHCID 14877952HCID 14877952, compound

Product 1

HCID 15678619HCID 15678619, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,3-bis(4-fluorophenyl)-2-(tetrazol-1-yl)2-propenol (108 mg, 0.34 mmol), triphenylphosphine (118 mg, 0.45 mmol) and N-bromosuccinimide (74 mg, 0.42 mmol) in tetrahydrofuran (5 mL) was stirred in an inert atmosphere for a period of 1.5 hours. The suspension (triphenylphosphine oxide precipitate) was diluted with hexanes (25 mL) and the suspension was filtered. The filtrate was concentrated under reduced pressure and the semi-crystalline solid was filtered through a short silica gel column eluted with 5-10% ethyl acetate in hexanes. The title compound, 108 mg.(84%), was obtained after removal of solvents under reduced pressure.

Workup

  1. filtrationthe suspension was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. filtrationthe semi-crystalline solid was filtered through a short silica gel column
  4. washeluted with 5-10% ethyl acetate in hexanes
  5. custom(84%), was obtained
  6. customafter removal of solvents under reduced pressure

Sources & evidence

ORD record
ord-b3877e0c5ee6433b98f3bae95c619563
Source dataset
uspto-grants-1991_12
Patent number
US05070206

Reaction notes

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