6-Bromopyridine-2-carbaldehyde → HCID 86602988, compound

HRID 2099560Notes

Reaction equation

HRID 2099560 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([Mg]Br)=[CH:13][CH:12]=1>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)[OH:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 178418676HCID 178418676, compound

Product 1

HCID 86602988HCID 86602988, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of the 6-Bromo-2-pyridine carboxaldehyde (6.12 g, 32.90 mmol) in anhydrous THF (150 mL) @ −78° C. under N2 was added 4-fluorophenylmagnesium bromide (2M in diethyl ether, 17.27 mL) dropwise. The reaction was warmed to 0° C. and stirred for 1.5 hr. The reaction was quenched with saturated aqueous NH4Cl. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated to give (6-bromopyridin-2-yl)(4-fluorophenyl)methanol. 1H NMR (500 MHz, CDCl3) δ 7.50 (t, 1H, J=7.7), 7.40 (d, 1H, J=7.8), 7.38-7.32 (m, 2H), 7.10 (d, 1H, J=7.6), 7.03 (t, 2H, J=8.7), 5.73 (d, 1H, J=4.2), 4.43 (d, 1H, J=4.4), LRMS m/z (M+H) Calcd.: 282.0, found: 282.0.

Workup

  1. custom@ −78° C. under N2
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. dry with materialThe combined organics were dried (anhd. Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aef1cb69aa8c4d77bab733673f7ba41a
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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