Benzoyl Peroxide → 1-(1-Bromoethyl)-4-fluorobenzene

HRID 1527023Notes

Reaction equation

HRID 1527023 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1)[CH3:2].C1C(=O)N([Br:17])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:17][CH:1]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1363031-Ethyl-4-fluorobenzene

Product 1

HCID 133890301-(1-Bromoethyl)-4-fluorobenzeneYield 81.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-ethyl-4-fluorobenzene (0.248 g, 2 mmol), NBS (0.35 g, 2 mmol) and benzoyl peroxide (0.14 g, 0.6 mmol) were dissolved in 20 mL CCl4, The mixture was stirred at 80° C. for 5 hours and then the reaction was conc. in vacuo and resulting oil was purified via silica gel chromatography (PE-EtOAC 5:1) to give the title compound (330 mg, 80%) as a yellow oil. LCMS 202 (M+H+).

Workup

  1. customresulting oil
  2. customwas purified via silica gel chromatography (PE-EtOAC 5:1)

Sources & evidence

ORD record
ord-91ac079668a2411595f4a355ba6b2756
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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