Benzyl Bromide → HCID 23034795, compound

HRID 1427024Notes

Reaction equation

HRID 1427024 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F:15][CH:16]([F:27])[O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][C:19]=1[OH:26]>C(#N)C>[CH2:7]([O:26][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:18]=1[O:17][CH:16]([F:15])[F:27])[CH:22]=[O:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehyde

Product 1

HCID 23034795HCID 23034795, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (3.91 g, 28.3 mmol) and benzyl bromide (2.5 mL, 21.1 mmol) were added to a solution of 4-(difluoromethoxy)-3-hydroxybenzaldehyde described in Production Example 19-1 (2.66 g, 14.2 mmol) in acetonitrile (50 mL) at room temperature, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered and then the solvent was evaporated. The resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-3:2). The target fraction was concentrated under vacuum and then the title compound was quantitatively obtained.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated
  3. customThe resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-3:2)
  4. concentrationThe target fraction was concentrated under vacuum

Sources & evidence

ORD record
ord-ab5234a3b5ea4604b4139aa2820da127
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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