Carbon tetrabromide → 2-(6-(Bromomethyl)pyridin-2-yl)propan-2-ol

HRID 876973Notes

Reaction equation

HRID 876973 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:12])([CH3:11])[CH3:10])[N:4]=1.C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].[Na+]>>[Br:14][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:12])([CH3:11])[CH3:10])[N:4]=1

Participants

5

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 191043162-(6-(Hydroxymethyl)pyridin-2-yl)propan-2-ol

Product 1

HCID 667183882-(6-(Bromomethyl)pyridin-2-yl)propan-2-olYield 74.2%

Procedure

To a solution of 2-hydroxymethyl-6-(1-hydroxy-1-methylethyl)pyridine (5.1 g, 30.5 mmol) in dicholoromethane (300 mL) was added carbon tetrabromide (8.81 g, 33.6 mmol) and triphenylphosphine (11.14 g, 33.6 mmol). The reaction was stirred at ambient temperature overnight then poured into a saturated solution of sodium bicarbonate. The organic layer was separated, concentrated to dryness and purified by column chromatography, eluting with a gradient of hexane to 3:1 hexane:ethyl acetate. The title compound (5.21 g, 74%) was obtained as a colourless oil; LC-MS Retention time 2.08 min, (M+H)+ 230, 232

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated to dryness
  3. custompurified by column chromatography
  4. washeluting with a gradient of hexane to 3:1 hexane

Sources & evidence

ORD record
ord-2fc48afee3264fc49925825c9a0f8002
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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