Ammonium Chloride → 1-(5-Bromopyridin-2-yl)ethanol

HRID 1520501Notes

Reaction equation

HRID 1520501 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[CH3:10][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:9])[CH3:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 98775625-Bromopyridine-2-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 426142881-(5-Bromopyridin-2-yl)ethanolYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-Bromo-pyridine-2-carbaldehyde (10 g, 53.76 mmol) in tetrahydrofuran (200 mL) at 0° C. is added drop wise methyl magnesium bromide (45 mL, 64.51 mmol). Reaction mixture is stirred 0° C. for 6 hours and diluted using saturated ammonium chloride solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by combiflash using 25% ethyl acetate in hexane as an eluent to give the title compound (8 g). 1H NMR (400 MHz, DMSO-d6) δ: 1.34 (d, J=6.52 Hz, 3H), 4.66-4.72 (m, 1H), 5.47 (d, J=4.76 Hz, 1H), 7.48 (d, 8.36 Hz, 1H), 8.021 (dd, J1=2.44 Hz, J2=8.44 Hz 1H), 8.58 (d, J=2.36 Hz, 1H). LC-Ms (m/z): 203.9 [M+H].

Workup

  1. customReaction mixture
  2. additiondiluted
  3. extractionextracted with ethyl acetate
  4. dry with materialOrganic layer is dried over sodium sulphate
  5. concentrationconcentrated
  6. custompurified by combiflash

Sources & evidence

ORD record
ord-f6af1e8c776840b7ab24e925035635c1
Source dataset
uspto-grants-2015_07
Patent number
US09073894B2

Reaction notes

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