Carbon tetrabromide → 3-Tert-butyldimethylsilyloxymethylbenzyl bromide

HRID 1179283Notes

Reaction equation

HRID 1179283 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:16]O)[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1>[Br:19][CH2:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 10658493(3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanol

Product 1

HCID 210978413-Tert-butyldimethylsilyloxymethylbenzyl bromideYield 14.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [3-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]methanol (J. Med. Chem. 1996, 25, 4871., 4.39 g, 17 mmol) and carbon tetrabromide (8.95 g, 27 mmol) in tetrahydrofuran (60 mL) was added triphenylphosphine (6.82 g, 26 mmol) in two portions at 0° C. and the mixture was stirred for 3 h at room temperature. The mixture was neutralized with aqueous sodium hydrogen carbonate and extracted with dichloromethane. The organic layer was concentrated. The residue was taken up in hexane and the resulting mixture was filtered, and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane/dichloromethane (10/1) to afford 760 mg (14%) of the title compound as a colorless oil:

Workup

  1. extractionextracted with dichloromethane
  2. concentrationThe organic layer was concentrated
  3. filtrationthe resulting mixture was filtered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/dichloromethane (10/1)

Sources & evidence

ORD record
ord-8e87220a0e1f4125a6241498bc963037
Source dataset
uspto-grants-2007_10
Patent number
US07279486B2

Reaction notes

Loading…