Tetrahydrofuran → (5-Bromo-2-chloro-3-methoxyphenyl)(4-ethylphenyl)methanone

HRID 576333Notes

Reaction equation

HRID 576333 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[C:5]([Cl:14])=[C:6]([CH:13]=1)[C:7](N(OC)C)=[O:8].C(O[C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1)C.[CH2:28]1COC[CH2:29]1>>[Br:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[C:5]([Cl:14])=[C:6]([C:7]([C:20]2[CH:21]=[CH:22][C:23]([CH2:28][CH3:29])=[CH:24][CH:25]=2)=[O:8])[CH:13]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 867140445-Bromo-2-chloro-N,3-dimethoxy-N-methylbenzamideHCID 178466691HCID 178466691, compound

Product 1

HCID 71110682(5-Bromo-2-chloro-3-methoxyphenyl)(4-ethylphenyl)methanoneYield 99%

Procedure

To a solution of compound 60 (3.45 g, 11.2 mmol) in THF (44 mL) was added dropwise 4-ethoxyphenyl magnesium bromide (0.5M in THF, 44.8 mL, 22.4 mmol) at 0° C. under an atmosphere of nitrogen. After being stirred for 15 hours at room temperature, the mixture was quenched with 1N HCl (10 mL). The mixture was extracted with EtOAc (100 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 61 (3.92 g, 99%) as a white solid.

Workup

  1. customthe mixture was quenched with 1N HCl (10 mL)
  2. extractionThe mixture was extracted with EtOAc (100 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-287b1cf985ce4132af5a6cde7821c7d2
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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