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

HRID 2209835Notes

Reaction equation

HRID 2209835 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17]([Si:21](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[O:7]([CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)[Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701194-Bromobenzyl alcoholHCID 94078tert-Butyldiphenylchlorosilane

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7.48 g (40 mmoles) of p-bromobenzyl alcohol and 6.07 g (60 mmoles) of triethylamine in 70 mL of sieve dried DMF at 0° C. was added 14.3 g (52 mmoles) of neat t-butyldiphenyl-silylchloride. The ice-water bath was removed and the mixture was stirred further for 20 hours. The mixture was partitioned between ether, ice-water, and 2N hydrochloric acid, and the organic phase was separated, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and evaporated.

Workup

  1. customThe ice-water bath was removed
  2. customThe mixture was partitioned between ether, ice-water, and 2N hydrochloric acid
  3. customthe organic phase was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3dbdb621b26842a2b5ec903cc9bbd01e
Source dataset
uspto-grants-1995_10
Patent number
US05455239

Reaction notes

Loading…