Imidazole → HCID 58007486, compound

HRID 2428095Notes

Reaction equation

HRID 2428095 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[Br:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:18])=[C:14]([CH2:16][OH:17])[CH:15]=1.N1C=CN=C1.[NH4+].[Cl-]>CN(C=O)C>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:18])=[C:14]([CH:15]=1)[CH2:16][O:17][Si:5]([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 5074766(5-Bromo-2-chlorophenyl)methanol

Product 1

HCID 58007486HCID 58007486, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

TBDMS-Cl (10.6 g, 66.7 mmol) was added to a sol. of (5-bromo-2-chloro-phenyl)-methanol (12.8 g, 55.6 mmol) and imidazole (9.42 g, 138 mmol) in DMF (190 mL) at 0° C. The mixture was stirred for 2 h at 0° C., and aq. sat. NH4Cl was added. The mixture was extracted with heptane (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane→EtOAc/heptane 1:49) yielded the title compound (18.0 g, 96%). LC-MS: tR=1.22 min.

Workup

  1. extractionThe mixture was extracted with heptane (2×)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (heptane→EtOAc/heptane 1:49)

Sources & evidence

ORD record
ord-5b2b22c7580f4b51935cbb5e0d14a47f
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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