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

HRID 1423034Notes

Reaction equation

HRID 1423034 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 8028TetrahydrofuranSolvent2×

Procedure

To a chilled (−10° C.) solution of 6-bromopyridine-2-carboxaldehyde (5.0 g, 27 mmol) in THF (108 mL) is added a 1 M solution of 4-fluorophenylmagnesium bromide in THF (30 mL, 30 mmol). The temperature is allowed to slowly warm to room temperature over 30 minutes and then the reaction mixture is quenched with saturated aqueous NH4Cl (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers are dried over Na2SO4 and concentrated. The crude material is purified by silica gel chromatography eluting with 15% EtOAc-hexanes to afford (6-bromopyridin-2-yl)-(4-fluorophenyl)-methanol.

Workup

  1. customthe reaction mixture is quenched with saturated aqueous NH4Cl (100 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude material is purified by silica gel chromatography
  6. washeluting with 15% EtOAc-hexanes

Sources & evidence

ORD record
ord-071abae634e2467799ffdf2ce8331205
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

Loading…