4-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-isopropylanisole → 4-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-isopropylphenol

HRID 1392552Notes

Reaction equation

[Br:1][C:2]1[C:19]([CH3:20])=[C:18]([N+:21]([O-:23])=[O:22])[CH:17]=[C:16]([Br:24])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11]C)=[C:7]([CH:13]([CH3:15])[CH3:14])[CH:6]=1>C(Cl)Cl>[Br:1][C:2]1[C:19]([CH3:20])=[C:18]([N+:21]([O-:23])=[O:22])[CH:17]=[C:16]([Br:24])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:13]([CH3:15])[CH3:14])[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-isopropylanisole of Part 8B (560-mg, 1.22 mmol) was dissolved in CH2Cl2 (10 mL) and cooled to 0° C. Ice-cold BF3-SMe2 (5 mL, 47.5 mmol) was added and the temperature was allowed to reach room temperature. After 16 hours stirring at room temperature, the reaction mixture was quenched by ice water and stirred for 30 minutes. A phase separator (IST) was used to separate the two phases and the aqueous phase was extracted by CHCl3. The collected organic phases were washed by brine and concentrated in vacuo. The residue was purified on column (MPLC, silica gel, gradient elution: n-heptane/EtOAc from 1:0 to 9:1) to give 250 mg (46%) of 4-(2,6-dibromo-3-methyl-4-nitrophenoxy)-2-isopropylphenol as light yellow syrup.

Workup

customto reach room temperature
customthe reaction mixture was quenched by ice water
stirringstirred for 30 minutes
customto separate the two phases
extractionthe aqueous phase was extracted by CHCl3
washThe collected organic phases were washed by brine
concentrationconcentrated in vacuo
customThe residue was purified on column (MPLC, silica gel, gradient elution: n-heptane/EtOAc from 1:0 to 9:1)

Sources & evidence

ORD record: ord-90d7951fe39e4491b72dbfac9ab71954
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342127B2

Reaction notes

Loading…