3-Bromo-2-fluorobenzaldehyde → HCID 86730397, compound

HRID 871138Notes

Reaction equation

HRID 871138 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[F:11][C:12]1[CH:17]=[CH:16][C:15]([Mg]Br)=[C:14]([O:20][CH3:21])[CH:13]=1>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[C:3]([F:10])=[C:4]([CH:5]([C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][C:14]=2[O:20][CH3:21])[OH:6])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 220193613-Bromo-2-fluorobenzaldehydeHCID 178492929HCID 178492929, compound2×

Product 1

HCID 86730397HCID 86730397, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-fluorobenzaldehyde (1.5 g, 7.39 mmol) in THF (Volume: 32.1 ml) cooled to 0° C. was added (4-fluoro-2-methoxyphenyl) magnesium bromide (17.73 ml, 8.87 mmol). After 50 min, additional (4-fluoro-2-methoxyphenyl)magnesium bromide (17.73 ml, 8.87 mmol) was added. The reaction was quenched with a saturated aqueous solution of NH4Cl. The reaction mixture was diluted with CH2Cl2. The layers were separated and the aqueous phase extracted with CH2Cl2 (2×). Organics combined, dried over Na2SO4, filtered, and concentrated to afford a yellow residue. The crude material was dissolved in a minimal amount of CH2Cl2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (80 g column, 60 mL/min, 0-30% EtOAc in hexanes over 30 min, tr=17 min) gave the title compound (2.10 g, 6.06 mmol, 82% yield) as a colorless liquid.

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of NH4Cl
  2. additionThe reaction mixture was diluted with CH2Cl2
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with CH2Cl2 (2×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow residue
  9. customto be chromatographed
  10. customPurification of the crude material by silica gel chromatography
  11. customan ISCO machine (80 g column, 60 mL/min, 0-30% EtOAc in hexanes over 30 min, tr=17 min)

Sources & evidence

ORD record
ord-f8efa8004ba941ad848b9edda47c7076
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

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