Boron tribromide → 2-(3-Isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile

HRID 636715Notes

Reaction equation

[CH:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[O:23]C)[O:7][C:8]1[C:15]([CH3:16])=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:9]=1[C:10]#[N:11])([CH3:3])[CH3:2].B(Br)(Br)Br>ClCCl>[CH:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[OH:23])[O:7][C:8]1[C:15]([CH3:16])=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:9]=1[C:10]#[N:11])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.), stirred solution of 2-(3-isopropyl-4-methoxy-phenoxy)-3-methyl-5-nitrobenzonitrile (308 mg) in dichloromethane (5 mL) was added boron tribromide (0.31 mL) dropwise. The reaction was allowed to warm to RT and stirred for 1 h, quenched with water and stirred for 20 min. The reaction was extracted with ethyl acetate, the organic phase washed with water, saturated aqueous brine, dried over sodium sulfate and concentrated in vacuo. Flash chromatography (20% ethyl acetate/hexanes) on silica gel afforded 2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile as a yellow oil (215 mg).

Workup

temperatureto warm to RT
customquenched with water
stirringstirred for 20 min
extractionThe reaction was extracted with ethyl acetate
washthe organic phase washed with water, saturated aqueous brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-120220b3c7d54ca9be48964a1e182d0a
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06194454B1

Reaction notes

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