Acetyl chloride → 2-Pyridinemethanol, 5-bromo-3-methoxy-, 2-acetate

HRID 445741Notes

Reaction equation

HRID 445741 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([CH2:8][O:9][C:19](=[O:21])[CH3:20])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 45361767(5-Bromo-3-methoxypyridin-2-yl)methanol

Product 1

HCID 596129932-Pyridinemethanol, 5-bromo-3-methoxy-, 2-acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (5-bromo-3-methoxy-pyridin-2-yl)-methanol (Stage 194.1.3, 2.79 mmol) and triethylamine (4.18 mmol) in dichloromethane was added slowly acetyl chloride (3.35 mmol) and the RM was stirred for 1 h at rt. The RM was diluted with dichloromethane, washed with saturated aqueous NaHCO3, with brine, dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by flash chromatography (heptane/EtOAc 0% to 60%). The fractions containing product were evaporated together to give the title compound as a white solid. (HPLC: tR 2.72 min (Method A); M+H=260, 262 MS-ES)

Workup

  1. washwashed with saturated aqueous NaHCO3, with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was absorbed on silica gel
  6. custompurified by flash chromatography (heptane/EtOAc 0% to 60%)
  7. additionThe fractions containing product
  8. customwere evaporated together

Sources & evidence

ORD record
ord-eb4f7e89be1d42329f07a66b68ff01d3
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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