Triethylamine → (4-Bromo-3-methylphenoxy)(tert-butyl)dimethylsilane

HRID 1181048Notes

Reaction equation

HRID 1181048 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].C(N(CC)CC)C.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:4][C:3]=1[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 728574-Bromo-m-cresol

Product 1

HCID 17984598(4-Bromo-3-methylphenoxy)(tert-butyl)dimethylsilaneYield 98.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A 12 L flask was charged with 4-bromo-3-methyl phenol (428 g, 2.29 mol), CH2Cl2 (7.5 L), triethylamine (480 mL, 3.45 mol), and tert-butyldimethylsilyl chloride (324 g, 2.15 mol). To the solution was added 4-dimethylaminopyridine (15.0 g, 0.123 mol). The reaction mixture was stirred at ambient temperature overnight. The reaction was washed with saturated ammonium chloride (2.2 L) and then DI water (0.9 L). The organic layer was dried (Na2SO4), filtered, and concentrated to crude product (699 g). This material was purified by silica gel chromatography (heptane) to give the title compound (637 g, 98.5%).

Workup

  1. washThe reaction was washed with saturated ammonium chloride (2.2 L)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to crude product (699 g)
  5. customThis material was purified by silica gel chromatography (heptane)

Sources & evidence

ORD record
ord-50cfdbef7ca0445b9cef3bd88b6f464a
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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