Triethylamine → HCID 22915149, compound

HRID 234226Notes

Reaction equation

HRID 234226 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([OH:13])=[C:7]([CH3:14])[C:3]=1[C:4]([OH:6])=[O:5].[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>C(#N)C>[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([O:13][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:22])[CH3:21])=[C:7]([CH3:14])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 22915050HCID 22915050, compound

Product 1

HCID 22915149HCID 22915149, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 12.0 g of 2-bromo-5-hydroxy-3-methoxy-6-methyl-benzoic acid in 700 ml of acetonitrile were added at -5° C. 27.7 g of tert-butyldimethylchlorosilane and 18.5 g of triethylamine. The mixture was stirred for 30 min at -5° C. and for 16 h at 20° C. The solvent was evaporated in vacuo and the solid residue was washed with water and dried in vacuo. A solution of this material in 200 ml of ethanol was heated for 8 h to 80° C. The solvent was evaporated in vacuo and the residue was recrystallized from pentane to yield 12.0 g of 2-bromo-5-(tert-butyl-dimethylsilanyloxy)-3-methoxy-6-methylbenzoic acid as white crystals, m.p. 120°-125° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. washthe solid residue was washed with water
  3. customdried in vacuo
  4. temperatureA solution of this material in 200 ml of ethanol was heated for 8 h to 80° C
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was recrystallized from pentane

Sources & evidence

ORD record
ord-6e80fc2e73b24f7086be873083f54646
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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