Acetone → 2-(6-Bromopyridin-2-yl)propan-2-ol

HRID 1969450Notes

Reaction equation

C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[N:14]=1.C(=O)=O.[CH3:23][C:24]([CH3:26])=[O:25].[Cl-].[NH4+]>C1COCC1>[Br:19][C:15]1[N:14]=[C:13]([C:24]([OH:25])([CH3:26])[CH3:23])[CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: -76 °C

Procedure

Place a 1.6 M solution of n-butyl lithium in hexane (31.2 mL, 50 mmol) in a dry 250 mL round bottomed flask fitted with a stir bar, septum and temperature probe. Cool in a dry-ice acetone bath to −76° C. Add THF (30 mL) to the solution, then add a solution of 2,6-dibromopyridine (11.5 g, 50 mmol) in THF (60 mL) slowly via syringe maintaining the temperature under −60° C. Stir the dark yellow-brown solution for 30 minutes in the dry-ice bath, then add acetone (6 mL, 80 mmol). Stir the deep green solution in the dry-ice bath for 15 minutes then allow the reaction to warm to room temperature. After an hour add a 5% aqueous solution of ammonium chloride (50 mL) carefully. Extract with dichloromethane, evaporate to give 2-(6-bromo-pyridin-2-yl)-propan-2-ol (10.6 g, 98%) as an orange oil. MS (m/z): 216 and 218 (M+H)+.

Workup

customfitted with a stir bar
temperaturemaintaining the temperature under −60° C
customthe reaction
temperatureto warm to room temperature
extractionExtract with dichloromethane
customevaporate

Sources & evidence

ORD record: ord-c8b34316ec7845f8aebad718a3d12861
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426448B2

Reaction notes

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