Triethylamine → 2-Bromo-4-(4-tert-butylphenyl)pyridine

HRID 2105605Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][N+:35]([O-])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].CCN(CC)CC>C(Cl)Cl.[Cl-].[Na+].O>[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][N:35]=[C:34]([Br:20])[CH:33]=2)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To triphenylphosphine (Aldrich) (2.4 g, 9.1 mmol) dissolved in 10 mL of CH2Cl2 in a 50-mL round-bottomed flask was added bromine (Aldrich) (0.43 mL, 8.5 mmol). After stirring at 0° C. for 10 min, 4-[4-(tert-butyl)phenyl]pyridine 1-oxide (1.5 g, 6.5 mmol) was added dropwise, followed by Et3N (1.2 mL, 8.5 mmol). The reaction mixture was stirred at 0° C. for 1 h and then at room temperature overnight. Methylene chloride and brine were added, and the aqueous layer was extracted with CH2Cl2. The organic layer was collected and dried over Na2SO4, filtered and concentrated in vacuo. Following purification by silica gel chromatography (10:1 hexane:EtOAc), the title compound was obtained as a pale yellow oil. MS (ESI, pos. ion) m/z: 293 (M+1).

Workup

stirringThe reaction mixture was stirred at 0° C. for 1 h
customat room temperature
customovernight
extractionthe aqueous layer was extracted with CH2Cl2
customThe organic layer was collected
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
custompurification by silica gel chromatography (10:1 hexane:EtOAc)

Sources & evidence

ORD record: ord-f8dd12d411a14dd498c9b89b4d2c6a9d
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579347B2

Reaction notes

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