1-Bromo-3-chloropropane → HCID 18507150, compound

HRID 1633549Notes

Reaction equation

CCCCCC.[H-].[Na+].[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[C:17]#[N:18])=[N:14][CH:15]=1.Br[CH2:28][CH2:29][CH2:30][Cl:31]>CN(C=O)C.CCOCC.O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)([CH2:28][CH2:29][CH2:30][Cl:31])[C:17]#[N:18])=[N:14][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of hexane washed 60% sodium hydride (0.35 g, 8.6 mmol) in DMF (2 mL) at 0° C. was added a solution of (5-bromo-pyridin-2-yl)-(3-methoxy-phenyl)-acetonitrile (1.75 g, 5.76 mmol) in DMF (5 mL). The reaction mixture was stirred at 0° C. for 30 min and at room temperature for 1 h. 1-bromo-3-chloropropane (0.69 mL, 6.91 mmol) was added and the mixture was stirred at room temperature for 4 h. To the reaction mixture was added H2O (5 mL) and Et2O and the organic layer was washed with brine (5×5 mL), dried over Na2SO4 and concentrated. Purification by flash chromatography with hexanes/EtOAc (10:1) yielded 1.81 g of 2-(5-bromo-pyridin-2-yl)-5-chloro-2-(3-methoxy-phenyl)-pentanenitrile. 1HNMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 7.76 (dd, 1H), 7.36 (d, 1h), 7.27-7.21 (m, 1H), 7.03 (d, 1H), 6.98 (s, 1H), 6.82 (dd, 1H), 4.77 (s, 3H), 3.55 (t, 2H), 2.79-2.70 (comp, 1H), 2.62-2.52 (comp, 1H), 1.89-1.79 (comp, 2H); MS (M+1) 378.8, 380.8.

Workup

stirringthe mixture was stirred at room temperature for 4 h
washthe organic layer was washed with brine (5×5 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
customPurification by flash chromatography with hexanes/EtOAc (10:1)

Sources & evidence

ORD record: ord-dffc19a70cf74752b470cd5e31ee7052
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503905B1

Reaction notes

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