Cyclohexyl bromide → 2-Cyclohexylnaphthalene

HRID 505945Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[Mg]Br.Br[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.CN(CCN(C)C)C.[Cl-].[NH4+]>>[CH:14]1([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

Reactant 4

HCID 7960Cyclohexyl bromide

HCID 8037N,N,N',N'-Tetramethylethylenediamine

HCID 25517Ammonium Chloride

HCID 178418423HCID 178418423, compound

Product 1

HCID 117904922-CyclohexylnaphthaleneYield 96%

Procedure

2-Naphthyl magnesium bromide (1.46 mL of 0.82 M-THF solution, 1.2 mmol) was added to a mixture of bromocyclohexane (163.1 mg, 1.0 mmol), FeCl3 (0.5 mL of 0.1 M-THF solution, 5 mol %) and TMEDA (181.1 μL, 1.2 mmol) at 25° C. over 20 minutes through an injection pump. After the addition of Grignard reagent mixture was completed, the reaction mixture was stirred for 10 minutes at this temperature. After treating with saturated aqueous ammonium chloride solution in a conventional manner, the reaction mixture was filtered through a pad of Florisil® and concentrated in vacuum. Using the internal standard (tetrachloroethane, 79 mg, 0.47 mmol), the crude product was analyzed by 1H NMR to give 2-cyclohexylnaphthalene in a yield of 96%.

Workup

filtrationthe reaction mixture was filtered through a pad of Florisil®
concentrationconcentrated in vacuum

Sources & evidence

ORD record: ord-60c0a9ce21d14832874c784c1706782a
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781599B2

Reaction notes

Loading…