Triethylamine → Silane, [(4-bromophenyl)methoxy](1,1-dimethylethyl)diphenyl-

HRID 1281223Notes

Reaction equation

HRID 1281223 reaction equation
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][OH:25])=[CH:22][CH:21]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl>[Si:1]([O:25][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([Br:19])=[CH:21][CH:22]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 701194-Bromobenzyl alcoholHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 14903624Silane, [(4-bromophenyl)methoxy](1,1-dimethylethyl)diphenyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tert-butyldiphenylsilyl chloride (10.4 mL, 40.1 mmol) was added to a solution of 4-bromobenzyl alcohol ( 5.0 g, 26.7 mmol) and 50 mL of dichloromethane. The solution was treated with triethylamine (3.72 mL, 26.7 mmol) and (dimethylamino)pyridine (163 mg, 1.34 mmol) and stirred overnight at room temperature. The solution was diluted with 300 mL of dichloromethane and washed with 50 mL of 10% aqueous HCl. The layers were separated and the aqueous layer was extracted with 50 mL of dichloromethane. The combined organic extracts were washed with brine, and dried (MgSO4), and filtered, and the solvents were removed in vacuo. The residue was filtered through a plug (6@X 2@) of silica gel using a solution of 97% hexane/ethyl acetate. After removal of the solvent the residue was heated under vacuum (3 torr) to 170° C. for 1 hour to remove a low-boiling impurity. The remaining material is the title compound.

Workup

  1. washwashed with 50 mL of 10% aqueous HCl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 50 mL of dichloromethane
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvents were removed in vacuo
  8. filtrationThe residue was filtered through a plug (6@X 2@) of silica gel using a solution of 97% hexane/ethyl acetate
  9. customAfter removal of the solvent the residue
  10. temperaturewas heated under vacuum (3 torr) to 170° C. for 1 hour
  11. customto remove a low-boiling impurity

Sources & evidence

ORD record
ord-0d255ecac99744fabec9969d80ffeca8
Source dataset
uspto-grants-2002_09
Patent number
US06452032B1

Reaction notes

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