4-Bromo-3-fluorobenzaldehyde → HCID 21696955, compound

HRID 379051Notes

Reaction equation

HRID 379051 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:10].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Mg]Br)=[CH:14][CH:13]=1>C(OCC)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([C:15]2[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=2)[OH:7])=[CH:4][C:3]=1[F:10]

Participants

4

Reactant 2

HCID 27834114-Bromo-3-fluorobenzaldehydeHCID 178478191HCID 178478191, compound

Product 1

HCID 21696955HCID 21696955, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Bromo-3-fluorobenzaldehyde (as described in Example 18, Step A) (3.61 g, 17.7 mmol) was dissolved in anhydrous diethyl ether (40 mL). To this solution was added a 1.0M solution of 4-chlorophenyl-magnesium bromide (21.3 mL, 21.3 mmol). After stirring at ambient temperature for 4 hr the reaction was quenched with satd. NH4Cl and extracted with Et2O. The organic layer was washed with satd NaHCO3 solution, water, brine, dried (MgSO4), concentrated and purified by chromatography (SiO2, 10% EtOAc/hexane) to give the title compound.

Workup

  1. customwas quenched with satd
  2. extractionNH4Cl and extracted with Et2O
  3. washThe organic layer was washed with satd NaHCO3 solution, water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by chromatography (SiO2, 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-33bfe88e8aec493780f85e0af7b32041
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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