Triethylsilane → 1-Bromo-4-(cyclopropylmethyl)benzene

HRID 2407467Notes

Reaction equation

HRID 2407467 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[CH2:12][CH2:11]2)O)=[CH:4][CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:10]2[CH2:11][CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 123566(4-Bromophenyl)(cyclopropyl)methanol

Product 1

HCID 116513971-Bromo-4-(cyclopropylmethyl)benzene

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(4-Bromophenyl)cyclopropylmethanol (15.0 g) is treated with triethylsilane (30 mL) and trifluoroacetic acid (30 mL) and stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure and the residue is purified by column chromatography (silica gel 230-400 mesh, ethyl acetate:n-hexane 3:97) to furnish 1-bromo-4-cyclopropylmethylbenzene.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue is purified by column chromatography (silica gel 230-400 mesh, ethyl acetate:n-hexane 3:97)

Sources & evidence

ORD record
ord-82a522c7101d43d89d12e42d8a444a55
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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