Diiodomethane → 4-Bromo-2-chloro-1-(1-methylcyclopropyl)benzene

HRID 855304Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:11])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([Zn]CC)C.FC(F)(F)C(O)=O.C(I)I.BrC1C=CC(C(C)=C)=C([Cl:37])C=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:11])[CH2:10][CH2:9]2)=[C:4]([Cl:37])[CH:3]=1

Participants

Reactant 5

HCID 6346Diiodomethane

HCID 6422Trifluoroacetic acid

HCID 573742501-Bromo-4-(1-methylcyclopropyl)benzene

HCID 578499374-Bromo-2-chloro-1-isopropenylbenzene

HCID 178418750HCID 178418750, compound

Product 1

HCID 693426514-Bromo-2-chloro-1-(1-methylcyclopropyl)benzeneYield 88%

Procedure

The title compound was synthesized in analogy to 1-bromo-4-(1-methylcyclopropyl)-benzene (described in example S87) using diethyl zinc (2.59 ml, 1M solution in hexane, 2.59 mmol), trifluoroacetic acid (200 μl, 2.59 mmol), CH2I2 (209 μl, 2.59 mmol) and 4-bromo-2-chloro-1-isopropenylbenzene (300 mg, 1.30 mmol). The isolated residue was purified by flash column chromatography (100% pentane) to give 4-bromo-2-chloro-1-(1-methylcyclopropyl)-benzene (280 mg, 88%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.48 (d, J=2.0 Hz, 1H), 7.30 (dd, J=2.0, 8.5 Hz, 1H), 7.22 (d, J=8.5 Hz, 1H), 1.32 (s, 3H), 0.81-0.73(m, 4H).

Workup

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

Sources & evidence

ORD record: ord-fed0807de11241acbc8d9ca1adf70f83
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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