Imidazole → ((5-Bromo-4-methyl-1,3-dihydroisobenzofuran-1-yl)oxy)(tert-butyl)dimethylsilan

HRID 1501868Notes

Reaction equation

HRID 1501868 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:9][C:10]1[C:11]([CH3:20])=[C:12]2[C:16](=[CH:17][CH:18]=1)[CH:15]([OH:19])[O:14][CH2:13]2.N1C=CN=C1>C(Cl)Cl>[Br:9][C:10]1[C:11]([CH3:20])=[C:12]2[C:16](=[CH:17][CH:18]=1)[CH:15]([O:19][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[O:14][CH2:13]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 867095385-Bromo-4-methyl-1,3-dihydroisobenzofuran-1-ol

Product 1

HCID 86709540((5-Bromo-4-methyl-1,3-dihydroisobenzofuran-1-yl)oxy)(tert-butyl)dimethylsilan

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of TBS-Cl (3.63 g, 24.10 mmol) in methylene chloride (15 mL) was added to a solution of 5-bromo-4-methyl-1,3-dihydroisobenzofuran-1-ol (2.76 g, 12.1 mmol) and imidazole (1.72 g, 25.3 mmol) in methylene chloride (80 mL) at 0° C., the resulting solution was stirred at rt overnight. The mixture was partitioned between DCM and water, the water phase was extracted with methylene chloride and the combined organic phase was dried over sodium sulfate then concentrated, and the residue was purified on silica gel column using ethyl acetatehexane to give the title compound. LC/MS: (M−131)+: 210.91; 212.91.

Workup

  1. customThe mixture was partitioned between DCM and water
  2. extractionthe water phase was extracted with methylene chloride
  3. dry with materialthe combined organic phase was dried over sodium sulfate
  4. concentrationthen concentrated
  5. customthe residue was purified on silica gel column

Sources & evidence

ORD record
ord-a5c0d10c654b475f918315c260deba67
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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