Lithium Bromide → (4-(Bromomethyl)phenoxy)(tert-butyl)dimethylsilane

HRID 1953383Notes

Reaction equation

HRID 1953383 reaction equation
FC(F)(F)C(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:9][CH:8]=1)=O.[Br-:23].[Li+]>C1COCC1.C(#N)C>[Si:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][Br:23])=[CH:8][CH:9]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 82050Lithium BromideHCID 99970054-{(t-Butyldimethylsilyl)oxy}benzyl trifluoroacetate

Product 1

HCID 10380115(4-(Bromomethyl)phenoxy)(tert-butyl)dimethylsilaneYield 88%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

The benzyl trifluoroacetate 8 (17.9 g) was dissolved in dry THF, and dry lithium bromide (5.06 g) was added with stirring. The mixture was refluxed overnight, cooled, diluted with acetonitrile, and extracted three times with hexane. The hexane layers were combined, dried, filtered, and concentrated, thereby leaving the product 10 as a white oil in 88% yield.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperaturecooled
  3. extractionextracted three times with hexane
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-caea78892fa840b9b949dda17bcf4585
Source dataset
uspto-grants-2000_09
Patent number
US06117845

Reaction notes

Loading…