Water → (3-Bromo-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)methanol

HRID 1969184Notes

Reaction equation

HRID 1969184 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+].O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([O:10][Si:11]([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:13])[CH3:12])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 577919013-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-benzaldehyde

Product 1

HCID 57791917(3-Bromo-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-benzaldehyde (7 g, 22.2 mmol) was dissolved in THF and sodium borohydride (0.92 g; 24.4 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and water was added, and the reaction mixture was partly evaporated to strip off THF. Ethyl acetate was added and the phases separated. The organic phase was washed with water, dried, and evaporated to dryness. Yield: 6.4 g; HPLC-MS: m/z: 317.0 (M+); Rt: 2.37 min.

Workup

  1. customthe reaction mixture was partly evaporated
  2. additionEthyl acetate was added
  3. customthe phases separated
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-d287ffcaf1d344a386912bb509b6fb9a
Source dataset
uspto-grants-2013_04
Patent number
US08426473B2

Reaction notes

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