Water → 2-(4-Methoxybenzyloxy)-3-bromo-4-methylpyridine

HRID 558460Notes

Reaction equation

HRID 558460 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1.[Br:13][C:14]1[C:15](Cl)=[N:16][CH:17]=[CH:18][C:19]=1[CH3:20].O>C1COCC1.CCOC(C)=O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:15]2[C:14]([Br:13])=[C:19]([CH3:20])[CH:18]=[CH:17][N:16]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 404251193-Bromo-2-chloro-4-methylpyridine

Product 1

HCID 670001042-(4-Methoxybenzyloxy)-3-bromo-4-methylpyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 60% NaH in mineral oil (0.290 g, 7.27 mmol) in THF (15 mL) at RT in a resealable pressure vessel was added (4-methoxyphenyl)methanol (0.906 ml, 7.27 mmol). After 5 minutes, 3-bromo-2-chloro-4-picoline (1.00 g, 4.84 mmol) was added and the mixture was heated to 75° C. After 1 hr, water was added and the mixture was diluted with EtOAc. After washing with water and brine, the organic fraction was dried with sodium sulfate and purified by silica gel chromatography using 0-30% EtOAc:hexanes to afford 2-(4-methoxybenzyloxy)-3-bromo-4-methylpyridine as a colorless oil. M+H+=308.0.

Workup

  1. waitAfter 1 hr
  2. washAfter washing with water and brine
  3. dry with materialthe organic fraction was dried with sodium sulfate
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-00729da3fd854147b1d35bcb61d2fdee
Source dataset
uspto-grants-2011_11
Patent number
US08063055B2

Reaction notes

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