Imidazole → HCID 21180673, compound

HRID 1386763Notes

Reaction equation

HRID 1386763 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11]O)[CH:5]=[CH:6][C:7]=1[F:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:37]I>CCOCC.CCOCC.CC#N>[I:37][CH2:11][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 211806993-(3,4-Difluorophenyl)propan-1-ol

Product 1

HCID 21180673HCID 21180673, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21885917Acetonitrile etherSolvent

Procedure

A solution of 2.00 g (11.6 mmol) of 3-(3,4difluorophenyl)propanol (from EXAMPLE 199, Step A), 3.96 g (15.1 mmol) of triphenylphosphine and 1.03 g (15.1 mmol) of imidazole in 2:1 v/v ether/CH3CN at 0° C. was treated with 4.10 g (16.3 mmol) of iodine. The resulting mixture was warmed to rt and stirred for 1 h. The mixture was diluted with 200 mL ether, and washed with sat'd Na2S2O3 (2×30 mL) and sat'd CuSO4 (30 mL). The organic phase was dried over MgSO4 and concentrated. The residue was partially dissolved in ether and filtered to remove triphenylphosphine oxide. The filtrate was concentrated. Flash chromatography on silica gel using 4:1 v/v hexanes/EtOAc afforded 3.25 g (99%) of the title compound.

Workup

  1. washwashed with sat'd Na2S2O3 (2×30 mL) and sat'd CuSO4 (30 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. dissolutionThe residue was partially dissolved in ether
  5. filtrationfiltered
  6. customto remove triphenylphosphine oxide
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a500c7d5fbb4460ebf6e1ccd11c1a3ae
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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