4-Iodo-1-tritylimidazole → HCID 21696984, compound

HRID 379053Notes

Reaction equation

HRID 379053 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Mg]Br)C.[Br:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)=[O:38])=[CH:33][C:32]=1[F:46]>C(Cl)Cl>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)([C:2]2[N:3]=[CH:4][N:5]([C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=2)[OH:38])=[CH:33][C:32]=1[F:46]

Participants

5

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 21696967HCID 21696967, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 21696984HCID 21696984, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Iodo-1-trityl-1H-imidazole (1.39 g, 3.18 mmol) was dissolved in anhydrous CH2Cl2 (10 mL). To this solution was added a 3.0M solution of ethylmagnesium bromide (1.11 mL, 3.34 mmol) and stirred under Ar. After 3 hr, a solution of (4-bromo-3-fluoro-phenyl)-(4-chloro-phenyl)-methanone (1.00 g, 3.18 mmol) dissolved in CH2Cl2 (5 mL) was added dropwise and the resulting solution was stirred overnight. The reaction was quenched with satd. NH4Cl solution, diluted with satd. NaHCO3 solution to pH=8.5, and extracted with CH2C2 (3×). The combined organic layers were dried (MgSO4), concentrated and purified using SiO2 chromatography (10-20% EtOAc/Hexane) to yield the title compound.

Workup

  1. additionwas added dropwise
  2. stirringthe resulting solution was stirred overnight
  3. customThe reaction was quenched with satd
  4. additionNH4Cl solution, diluted with satd
  5. extractionNaHCO3 solution to pH=8.5, and extracted with CH2C2 (3×)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated
  8. custompurified

Sources & evidence

ORD record
ord-1e3497109b914cd7863cec51449514d6
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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