Diiodomethane → 4-Iodo-2-methyl-1,1'-biphenyl

HRID 1701010Notes

Reaction equation

N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([CH3:14])[CH:3]=1.N(OCCC(C)C)=O.[I:23]CI>>[I:23][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([CH3:14])[CH:3]=1

Participants

Reactant 3

HCID 6346Diiodomethane

HCID 8053Isoamyl Nitrite

HCID 443032-Methyl[1,1'-biphenyl]-4-amine

Product 1

HCID 108917094-Iodo-2-methyl-1,1'-biphenylYield 66%

Conditions

Temperature: 75 °C

Procedure

A stirred solution of 4-amino-2-methyl-1-phenylbenzene (10.49 gm, 57.2 mmol) in diiodomethane (100 mL) was treated with iso-amyl nitrite (27 mL, 200.2 mmol) over 5 mins. The mixture was heated to 75° C. for 45 mins, then at 65° C. for 1 h. After being cooled, the mixture was concentrated under reduced pressure (95° C./30 mmHg) and the residue was purified by flash chromatography (eluting with hexane) to give 4-iodo-2-methyl-1-phenylbenzene (11.6 gm, 66%) as an oil.

Workup

temperatureAfter being cooled
concentrationthe mixture was concentrated under reduced pressure (95° C./30 mmHg)
customthe residue was purified by flash chromatography (eluting with hexane)

Sources & evidence

ORD record: ord-d30b894500a049bb9da7855f4feb1001
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350907B1

Reaction notes

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