Water → 4-Fluoro-3-(pyridin-2-yl)benzaldehyde

HRID 594216Notes

Reaction equation

HRID 594216 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][C:10]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][C:10]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

9

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 2763240(2-Fluoro-5-formylphenyl)boronic acid

Product 1

HCID 636811574-Fluoro-3-(pyridin-2-yl)benzaldehyde

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of commercially available 2-bromopyridine (250 mg; 1.58 mmol), 2-fluoro-5-formylphenylboronic acid (265 mg; 1.58 mmol), and Pd(PPh3)4 (91 mg; 0.08 mmol) in toluene (1 ml), EtOH (1 ml), and aq. 2 M Na2CO3 (1.5 ml) was heated to 80° C., under nitrogen, for 17 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=7/3) afforded 4-fluoro-3-(pyridin-2-yl)benzaldehyde as a slightly yellow oil. LC-MS (conditions A): tR=0.51 min.; [M+H]+: 202.05 g/mol.

Workup

  1. temperatureAfter cooling to rt
  2. extractionThe separated aq. layer was further extracted with AcOEt
  3. washThe mixed organic layers were washed with brine
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (heptane/AcOEt=7/3)

Sources & evidence

ORD record
ord-54723c84643546c8a82b7708295c323d
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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