Dimethyl Sulfide → HCID 18380364, compound

HRID 2299977Notes

Reaction equation

[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([N:7]2[CH:11]=[CH:10][CH:9]=[CH:8]2)=[CH:3][CH:2]=1.CSC.C(#N)C.[Br:24]Br>C(Cl)Cl>[C:1]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][C:4]([N:7]2[CH:11]=[CH:10][C:9]([Br:24])=[CH:8]2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To a mixture of N-biphenyl-4-yl-1H-pyrrole (500 mg, 2.28 mmol), dimethylsulfide (0.25 mL, 3.4 mmol), CH2Cl2 (30 mL), and acetonitrile (10 mL) at −10° C. was added dropwise a solution of bromine in CH2Cl2 (5 mL) over 15 minutes. The mixture was allowed to warm to 10° C. over 2 hours. The resultant mixture was washed with 1M pH 7 phosphate buffer (50 mL) and extracted with CH2Cl2 (25 mL). The combined organic layers were dried over Na2SO4 and concentrated to a crude residue which was purified via flash column chromatography with 0-10% CH2Cl2/hex gradient eluant to furnish 240 mg(40%) of N-(biphenyl-4-yl)-3-bromo-1H-pyrrole as a white solid, mp 141-3° C. 1H NMR: δ 7.65 (d, 2H, J=8.5 Hz), 7.59 (d, 2H, J=8.1 Hz), 7.49-7.34 (m, 5H), 7.12 (s, 1H), 7.02 (t, 1, J=2.6 Hz), 6.36 (dd, 1H, J=3.2, 1.7 Hz). Anal. Calculated for C16H12NBr: C, 64.45; H, 4.06; N, 4.70; Br, 26.80. Found: C, 64.37; H, 4.10; N, 4.64; Br, 26.69.

Workup

washThe resultant mixture was washed with 1M pH 7 phosphate buffer (50 mL)
extractionextracted with CH2Cl2 (25 mL)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated to a crude residue which
customwas purified via flash column chromatography with 0-10% CH2Cl2/hex gradient eluant

Sources & evidence

ORD record: ord-148b775124514fa8b5ce6c4597b627b6
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495699B2

Reaction notes

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