Imidazole → 1-(Tert-butyldiphenylsilyloxymethyl)-2,6-dichloro-3-nitrobenzene

HRID 636473

Reaction equation

HRID 636473 reaction equation
[Cl:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[C:3]=1[CH2:4][OH:5].N1C=CN=C1.[Si:19](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.O>[Si:19]([O:5][CH2:4][C:3]1[C:6]([Cl:13])=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=1[Cl:1])([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2794914(2,6-Dichloro-3-nitrophenyl)methanol

Product 1

HCID 117981851-(Tert-butyldiphenylsilyloxymethyl)-2,6-dichloro-3-nitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dichloro-3-nitrobenzyl alcohol (5.0 g) in N,N-dimethylformamide (25 ml) were added imidazole (1.69 g) and tert-butyldiphenylsilyl chloride (6.0 ml) at ambient temperature with stirring. After 8 hours, the mixture was diluted with water (25 ml) and was extracted with ethyl acetate twice. The organic layer was washed with water and brine, dried over magnesium sulfate. The solvent was removed in vacuo to give 1-(tert-butyldiphenylsilyloxy-methyl)-2,6-dichloro-3-nitrobenzene (11.5 g) as an oil.

Workup

  1. extractionwas extracted with ethyl acetate twice
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d0f516dca2d644df921aba87cd07eca9
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Linked notes

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