Triethylsilane → 5-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran

HRID 858595Notes

Reaction equation

HRID 858595 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8](O)[C:7]([CH3:12])([CH3:11])[C:6]=2[CH:13]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:12])[C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 205362245-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuranHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran-2-ol (813 mg, 3.36 mmol), Triethylsilane (805 □L, 5.04 mmol), and 30% TFA/CH2Cl2 (15 mL), were stirred at room temperature for 1 h. The solution was then diluted with Toluene (15 mL), stripped of all solvents, and chromatographed on silica eluted with a gradient 5–25% Ethyl acetate/Hexanes. Yield 549 mg, 72%.

Workup

  1. customchromatographed on silica
  2. washeluted with a gradient 5–25% Ethyl acetate/Hexanes

Sources & evidence

ORD record
ord-016d0070ac094b71acdf0328e0163ead
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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