Phosphorus oxybromide → 4-Bromo-2-tert-butylpyridine

反応式

[C:1]([C:5]1[NH:6][CH:7]=[CH:8][C:9](=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].P(Br)(Br)([Br:14])=O>>[Br:14][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1

参加物

反応物 2

HCID 24613Phosphorus oxybromide

HCID 582800252-Tert-butylpyridin-4(1H)-one

生成物 1

HCID 457878674-Bromo-2-tert-butylpyridine収率 86.4%

反応条件

温度: 120 °C

実験手順

A mixture of 2-tert-butyl-1H-pyridin-4-one (Step 1.5) (4.25 g, 28 mmol) and POBr3 (8.88 g, 31 mmol, 1.1 eq) is heated to 120° C., stirred for 15 min, allowed to cool, quenched by addition of a saturated solution of NaHCO3 and extracted with DCM/MeOH (9:1, v/v). The organic phase is washed with a saturated solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/EtOAc, 95:5) to afford 5.18 g of the title compound as a yellow oil: ESI-MS: 214.0/216.0 [M+H]+; tR=2.49 min (System 1); TLC: Rf=0.35 (Hex/EtOAc, 1:1).

後処理

temperatureto cool
customquenched by addition of a saturated solution of NaHCO3
extractionextracted with DCM/MeOH (9:1
washThe organic phase is washed with a saturated solution of NaHCO3
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue is purified by silica gel column chromatography (Hex/EtOAc, 95:5)

出典と根拠

ORDレコード: ord-84920b5a330c426ab04d0ab61fd77d76
出典データセット: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08980259B2

反応ノート

読み込み中…

参加物