Phosphorus tribromide → (4-(Bromomethyl)-2-ethoxyphenoxy)(tert-butyl)dimethylsilane

HRID 718541Notes

Reaction equation

HRID 718541 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][C:10]=1[O:17][CH2:18][CH3:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].P(Br)(Br)[Br:21].C([O-])(O)=O.[Na+]>>[Br:21][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:10]([O:17][CH2:18][CH3:19])[CH:11]=1

Participants

4

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 67984855(4-(Tert-butyldimethylsilyloxy)-3-ethoxyphenyl)methanol

Product 1

HCID 67984658(4-(Bromomethyl)-2-ethoxyphenoxy)(tert-butyl)dimethylsilaneYield 94.6%

Conditions

Temperature
0 °C

Procedure

To a solution of (4-(tert-butyldimethylsilyloxy)-3-ethoxyphenyl)methanol (12.5 g, 44.4 mmol, 1.0 equiv.) in CH2CI2 (45 mL), PBr3 (5.0 mL, 53.2 mmol, 1.2 equiv.) was added at 0° C., and the mixture was stirred at 0° C. for 30 min. After slow addition of sat. aq. NaHCO3-solution, the aqueous layer was extracted with CH2Cl2 (2×). The combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated to yield 14.5 g (94%) of (4-(bromomethyl)-2-ethoxyphenoxy)(tert-butyl)dimethylsilane as a light yellow oil.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7bc6aaf14a8749c2bf42b8aa4cdcfe69
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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