1,4-Dibromobenzene → HCID 13328634, compound

HRID 628207Notes

Reaction equation

[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.[CH3:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19]>C1COCC1>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:15]([OH:20])([CH3:14])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: -78 °C

Procedure

n-BuLi (2.5 M in hexanes, 17.0 mL, 42.5 mmol) was added dropwise to a solution of 1,4-dibromobenzene (10.04 g, 42.5 mmol) in THF (100 mL) at −78° C. under nitrogen. After stirring at −78° C. for 1 hour, 2-hexanone (4.5 g, 44.9 mmol) was added dropwise, and the solution was warmed to room temperature and stirred overnight. The reaction mixture was quenched with water and the organic layer was separated. Next, the organic phase was washed with water, dried over Na2SO4, and concentrated on a rotary evaporator to give a crude oil. The crude was purified by column chromatography (silica gel, chloroform) to give 6 as a colorless oil (10.0 g, 91% yield). 1H NMR (500 MHz, CDCl3) δ 7.45 (d, J=8.8 Hz, 2H), 7.30 (d, J=8.8 Hz, 2H), 1.79-1.75 (m, 2H), 1.68 (s, 1H), 1.54 (s, 3H), 1.24-1.28 (m, 4H), 0.85 (t, 3H).

Workup

temperaturethe solution was warmed to room temperature
stirringstirred overnight
customThe reaction mixture was quenched with water
customthe organic layer was separated
washNext, the organic phase was washed with water
dry with materialdried over Na2SO4
concentrationconcentrated on a rotary evaporator
customto give a crude oil
customThe crude was purified by column chromatography (silica gel, chloroform)

Sources & evidence

ORD record: ord-8ed7c348c1034c0bafb3a51ce9ff7dce
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09312501B2

Reaction notes

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