Water → HCID 67348552, compound

HRID 1671277Notes

Reaction equation

HRID 1671277 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=1[CH:12]=[O:13].O>O1CCCC1>[F:9][C:10]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=1[CH:12]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:13]

Participants

5

Reactant 3

HCID 962WaterHCID 27348722-Fluoro-5-methoxybenzaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 67348552HCID 67348552, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenylmagnesium bromide (1.6 mL, 1.0 M tetrahydrofuran solution, manufactured by Kanto Chemical Co., Inc.) was added to a solution of 2-Fluoro-5-methoxybenzaldehyde (500 mg, manufactured by Tokyo Chemical Industry Co., Ltd.) in tetrahydrofuran (16 mL, manufactured by Wako Pure Chemical Industries, Ltd.) at 0° C., and the mixture was stirred overnight at room temperature. Water (10 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (3×20 mL), washed with brine (20 mL) and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1), to give 480 mg of the title compound. LC-MS: HPLC retention time 3.90 minutes, m/z 233 (M+H), condition B-1.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  2. washwashed with brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was then evaporated
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-50a4cfe7b5604f9ca6807f8139e071fa
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

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