Benzene → 1-Bromo-4-ethylbenzene

HRID 431700Notes

Reaction equation

HRID 431700 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9](C)(C)[CH3:10])=[C:6](O)[CH:7]=1.C1C=CC=CC=1.CC(C)([O-])C.[K+].BrC1C=CC(CC)=CC=1[N+]([O-])=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][CH3:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 53260741-Bromo-4-ethyl-2-nitrobenzeneHCID 103313825-Bromo-2-tert-butylphenol4×HCID 23665647Potassium tert-butoxide

Product 1

HCID 153131-Bromo-4-ethylbenzene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Employing the same general procedure as for the preparation of 5-bromo-2-tert-butyl-1-[(2′-amino-4′-methyl)phenoxy]benzene (Compound I), 781 mg (3.4 mmol) of 5-bromo-2-tert-butylphenol (Compound H) was converted into crude 5-bromo-2-tert-butyl-1-[4′-ethyl-2′-nitro)phenoxy]benzene using 611 mg (5.0 mmol) of potassium t-butoxide, 1.0 g (5.25 mmol) of cuprous iodide, 770 mg (˜2.78 mmol) of 1-bromo-4-ethyl-2-nitrobenzene (80% purity, obtained from the nitration of 1-bromo-4-ethylbenzene) and 10 mL of pyridine. Purification by flash chromatography (silica, 5% ethyl acetate in hexane) gave crude 5-bromo-2-tert-butyl-1-[(4′-methyl-2′-nitro)phenoxy]benzene as a yellow oil. 290 mg of this crude sample was converted into the title compound using a balloon filled with hydrogen, 31 mg of 10% Pd/C, 4 mL of acetonitrile and 1 mL of methanol. Purification by flash chromatography (silica, 2% ethyl acetate in hexane) gave the title compound as a yellow oil.

Sources & evidence

ORD record
ord-d2b3a2bcfcd9485586f14139c0e3b5a9
Source dataset
uspto-grants-2003_12
Patent number
US06660755B2

Reaction notes

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