Water → 4-broMo-2-fluoro-5-Methoxy-benzaldehyde

HRID 858705Notes

Reaction equation

HRID 858705 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:5]=1[CH:6]=[O:7].O>C(Cl)(Cl)Cl>[Br:1][C:10]1[C:9]([O:12][CH3:13])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:3])[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 575272884-broMo-2-fluoro-5-Methoxy-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine (15 ml, 300 mmol) was added slowly to a solution of 2-Fluoro-5-methoxy-benzaldehyde (23.12 g, 150 mmol) in chloroform (500 ml), and the mixture was stirred at room temperature for 5 days. The mixture was poured into water (200 ml) and extracted with chloroform (2×200 mL). The organics were washed with water (200 mL) and brine (200 mL), dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (2–16% EtOAc in hexanes) to give the product. Yield: 20.7 g, 60%. 1H NMR (CDCl3) δ: 3.93 (s, 3H), 7.08–7.13 (m, 1H), 7.29 (d, J=12.4 Hz, 1H).

Workup

  1. extractionextracted with chloroform (2×200 mL)
  2. washThe organics were washed with water (200 mL) and brine (200 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (2–16% EtOAc in hexanes)
  7. customto give the product

Sources & evidence

ORD record
ord-719671dc778d4fc4a982b6bf6291feae
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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