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

HRID 379049Notes

Reaction equation

HRID 379049 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

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromo-3-fluorobenzaldehyde (1.6 g, 7.88 mmol) in diethylether (20 mL) at 0° C. was added 4-chlorophenyl-magnesiumbromide (1Mether, 9.46 mL, 9.46 mmol) dropwise via syringe. The cooling bath was removed and after the mixture was stirred for 18 hr it was cooled to 0° C. and saturated NH4Cl solution (20 mL) was added to quench the reaction. The reaction mixture was partitioned between EtOAc and saturated NaHCO3 solution. The EtOAc layer was washed with H2O, brine, and dried (MgSO4). Filtration and concentration in vacuo gave the title compound as a solid after chromatography (silica gel, hexane:EtOAc/85:15).

Workup

  1. customThe cooling bath was removed
  2. additionsaturated NH4Cl solution (20 mL) was added
  3. customto quench
  4. customthe reaction
  5. customThe reaction mixture was partitioned between EtOAc and saturated NaHCO3 solution
  6. washThe EtOAc layer was washed with H2O, brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-25754b29e4254f88882963ad38949b42
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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