2-Phenylethanol → 1-Iodo-3-(phenethoxymethyl)benzene

HRID 2095334Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[I:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br>O1CCCC1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[I:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:15]([CH2:16][O:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Into a 100 mL round-bottom flask was placed under N2 a solution of 2-phenylethanol (110 mg, 0.90 mmol) in tetrahydrofuran (10 mL). Sodium hydride (26 mg, 1.08 mmol, 1.2 equiv.) was added with ice cooling. The mixture was stirred for 2 h at 25° C., then 3-iodobenzyl bromide (320 mg, 1.08 mmol, 1.2 equiv.) and n-Bu4NBr (30 mg, 0.09 mmol, 0.10 equiv.) were added. The resulting solution was stirred for 20 h at 25° C. The reaction progress was monitored by TLC (SiO2, EtOAc/petroleum ether 1:5). The reaction was quenched by the addition of saturated aqueous NH4Cl solution. The resulting solution was extracted with EtOAc, and the organic layers were combined, dried over Na2SO4, and concentrated under vacuum. The residue was chromatographed on silica gel with EtOAc/petroleum ether 1:20 to obtain 300 mg (99%) of 1-iodo-3-(phenethoxymethyl)benzene as a yellow oil.

Workup

customInto a 100 mL round-bottom flask was placed under N2
stirringThe resulting solution was stirred for 20 h at 25° C
customThe reaction was quenched by the addition of saturated aqueous NH4Cl solution
extractionThe resulting solution was extracted with EtOAc
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customThe residue was chromatographed on silica gel with EtOAc/petroleum ether 1:20

Sources & evidence

ORD record: ord-8afacb9fdaab4e28a0f430e930806244
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445684B2

Reaction notes

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