3-Chlorophenol → HCID 21697000, compound

HRID 379055Notes

Reaction equation

HRID 379055 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:42])([C:18]2[N:19]=[CH:20][N:21]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:22]=2)[C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11](F)[CH:10]=2)=[CH:4][CH:3]=1.[Cl:43][C:44]1[CH:45]=[C:46]([OH:50])[CH:47]=[CH:48][CH:49]=1.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>CC#N>[Cl:43][C:44]1[CH:45]=[C:46]([CH:47]=[CH:48][CH:49]=1)[O:50][C:11]1[CH:10]=[C:9]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:42])[C:18]2[N:19]=[CH:20][N:21]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:22]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

6

Reactant 4

HCID 79333-ChlorophenolHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 21697016HCID 21697016, compound

Product 1

HCID 21697000HCID 21697000, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-[(4-Chloro-phenyl)-hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-2-fluoro-benzonitrile (0.337 g, 0.591 mmol), 3-chlorophenol (0.074 mL, 0.709 mmol), 40% KF on alumina (0.182 g), and 18-Crown-6 ether (0.018 g, 0.068 mmol) were refluxed in CH3CN for 40 hr under Ar. The reaction mixture was concentrated in vacuo, diluted with EtOAc, washed with satd. NaHCO3 solution, water, brine and dried (MgSO4). Filtration and concentration gave the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed with satd
  4. dry with materialNaHCO3 solution, water, brine and dried (MgSO4)
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-dce06a0492004d33958660af084a7630
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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