Diiodomethane → 1-Bromo-4-(1-ethylcyclopropyl)-benzene

HRID 855276Notes

Reaction equation

HRID 855276 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(OC)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[C:14]1C=C(Cl)C=C(Cl)[C:15]=1O.C([Zn]CC)C.C(I)I.BrC1C=CC(C(=C)CC)=CC=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH3:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 6346DiiodomethaneHCID 69142,4,6-TrichlorophenolHCID 221662261-Bromo-4-(but-1-en-2-yl)benzeneHCID 22568990HCID 22568990, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 693421551-Bromo-4-(1-ethylcyclopropyl)-benzeneYield 85%

Procedure

The title compound was synthesized in analogy to 1-bromo-4-(1-methoxycyclopropyl)-benzene (described in example S89) using 2,4,6-trichlorophenol (580 mg, 2.94 mmol), diethyl zinc (2.94 ml, 1M solution in hexane, 2.94 mmol), CH2I2 (237 μl, 2.94 mmol) and 1-bromo-4-(1-methylenepropyl)-benzene (310 mg, 1.47 mmol). The isolated residue was purified by flash column chromatography (100% pentane) to give 1-bromo-4-(1-ethylcyclopropyl)-benzene (280 mg, 85%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.39 (d, J=8.5 Hz, 2H), 7.16 (d, J=8.5 Hz, 2H), 1.55 (q, J=7.5 Hz, 2H), 0.82 (t, J=7.5 Hz, 3H), 0.75-0.71(m, 2H), 0.68-0.64 (m, 2H).

Workup

  1. customThe isolated residue was purified by flash column chromatography (100% pentane)

Sources & evidence

ORD record
ord-57445dfee53843f298db030c840f3ed6
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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