Tetrahydrofuran → 4-(4-Bromophenethyl)-1-methoxybenzene

HRID 476334Notes

Reaction equation

HRID 476334 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7]Br)=[CH:4][CH:3]=1.C1COCC1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1>CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][C:21]2[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 110108254-Bromophenethyl bromideHCID 178491912HCID 178491912, compound2×

Product 1

HCID 135480814-(4-Bromophenethyl)-1-methoxybenzene

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-Bromophenethyl bromide (261.4 mg, 1.0 mmol) and a THF solution (1.42 mL, 1.06 M, 1.5 mmol) of 4-methoxyphenylmagnesium bromide were used as starting materials, and reacted as in Entry 1. Conditions: The THF solution of 4-methoxyphenylmagnesium bromide was added dropwise at 40° C. over 3 hours. After thin-layer chromatography (hexane/ethyl acetate=92/8), the title compound was obtained as a colorless liquid (0.226 g, yield 78%).

Workup

  1. custommaterials, and reacted as in Entry 1

Sources & evidence

ORD record
ord-20fcc1df6c73470c853001b20beeb23b
Source dataset
uspto-grants-2014_01
Patent number
US08637710B2

Reaction notes

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