4-Bromophenol → Silane, (4-bromophenoxy)(1,1-dimethylethyl)diphenyl-

HRID 2253750Notes

Reaction equation

HRID 2253750 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Si:9](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN(CC)CC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[O:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[Si:9]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 8471TriethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 11292808Silane, (4-bromophenoxy)(1,1-dimethylethyl)diphenyl-

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromophenol (16.4 g, 0.1 mole) in CH2Cl2 (300 mL) was added t-butyldiphenylsilyl chloride (29 g, 0.1 mole), Et3N (20 g, 0.2 mole) and 4-dimethylaminopyridine (DMAP) (1 g). The solution was stirred at RT for 2 days, quenched with H2O (1L) and extracted with ether (2L). The ether extracts were dried and evaporated. Flash chromatography of the residue using 5% ethyl acetate in hexane afforded the title compound which was used as such for the next step.

Workup

  1. customquenched with H2O (1L)
  2. extractionextracted with ether (2L)
  3. dry with materialThe ether extracts were dried
  4. customevaporated

Sources & evidence

ORD record
ord-7e3c9f7755bb44b4a51a4673a0e98af6
Source dataset
uspto-grants-1993_08
Patent number
US05232916

Reaction notes

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