2-Bromo-4-fluorobenzaldehyde → HCID 57445089, compound

HRID 558134Notes

Reaction equation

HRID 558134 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][Mg]Br.[Br:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH:14]=[O:15]>C1COCC1>[Br:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH:14]([OH:15])[CH2:8][CH2:7][CH:2]1[O:3][CH2:4][CH2:5][CH2:6][O:1]1

Participants

4

Reactant 2

HCID 27733192-Bromo-4-fluorobenzaldehydeHCID 178419673HCID 178419673, compound

Product 1

HCID 57445089HCID 57445089, compoundYield 511.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add (1,3-dioxan-2-ylethyl)magnesium bromide (0.5 M in THF, 40 mL, 20 mmol) to a solution of 2-bromo-4-fluoro-benzaldehyde (3 g, 15 mmol) in THF (20 mL) at 0° C. under N2. Continue to stir the mixture for 48 h at RT. Quench the reaction mixture with 1 N HCl, followed by the basification with diluted ammonium hydroxide to ˜pH 9. Extract the product with chloroform/IPA (3/1). Dry the organic layer over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (10% methanol in DCM) to give the title compound as a yellow oil (24.5 g, 95%). MS (ES) m/z 319/321 [M+1]+.

Workup

  1. customQuench the reaction mixture with 1 N HCl
  2. extractionExtract the product with chloroform/IPA (3/1)
  3. dry with materialDry the organic layer over sodium sulfate
  4. concentrationConcentrate the solution in vacuo
  5. customPurify by column chromatography (10% methanol in DCM)

Sources & evidence

ORD record
ord-32522a0d94ab4d5095da2f356ffad27e
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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