tert-Butyldimethylsilyl chloride → HCID 131734205, compound

HRID 1497496Notes

Reaction equation

HRID 1497496 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21]>ClCCl.CN(C1C=CN=CC=1)C.O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11]

Participants

6

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 89451820HCID 89451820, compound

Product 1

HCID 131734205HCID 131734205, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl (2-bromo-4-hydroxyphenyl)acetate (2.00 g) in dichloromethane (30.0 mL) were added tert-butyl (chloro)dimethylsilane (1.13 g) and N,N-dimethyl-4-aminopyridine (913 mg) under ice-cooling, followed by stirring for 2 hours under ice-cooling. The reaction mixture was diluted with water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain benzyl (2-bromo-4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)acetate (2.63 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-333048c1f47b46fdaddba108571a970b
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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