Methanol → (5-Bromo-4-chloropyridin-2-yl)methanol

HRID 1655222Notes

Reaction equation

HRID 1655222 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:10])[N+:5]([O-])=[CH:6][C:7]=1[Br:8].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:14].CO.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[Cl:1][C:2]1[C:7]([Br:8])=[CH:6][N:5]=[C:4]([CH2:10][OH:14])[CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 136827785-Bromo-4-chloro-2-methylpyridine 1-oxide

Product 1

HCID 19791171(5-Bromo-4-chloropyridin-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-5-bromo-2-picoline-N-oxide (23.9 g) in dichloromethane (250 ml) was cooled to 10° and trifluoroacetic anhydride (25 ml) added over 20 minutes. The mixture was allowed to warm to ambient temperature, and stand for 7 days. After cooling to 10°, methanol (100 ml) was added, and the solution stripped. The residue was treated with water (150 ml), basified with saturated aqueous sodium carbonate to pH 10, and extracted with ethyl acetate (2×150 ml). The combined extracts were dried (MgSO4). stripped, and triturated with ether to give 4-chloro-5-bromo-2-hydroxymethylpyridine, 16.58 g. m.p. 109°-10°.

Workup

  1. temperatureAfter cooling to 10°
  2. extractionextracted with ethyl acetate (2×150 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customtriturated with ether

Sources & evidence

ORD record
ord-e163051bcfda47bca66e9cf94ce700db
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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