Hydrochloric Acid → 2-Bromo-6-fluorobenzaldehyde

HRID 2404370Notes

Reaction equation

HRID 2404370 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[Li+].CCC[CH2-].C(NC(C)C)(C)C.Cl.C1C[O:33][CH2:32]C1>O.CC(OC)(C)C.C(O)(=O)C.CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:32]=[O:33]

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 140821-Bromo-3-fluorobenzeneHCID 61028n-Butyl lithiumHCID 2724682Lithium diisopropylamide

Product 1

HCID 224739772-Bromo-6-fluorobenzaldehyde

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

1-Bromo-3-fluorobenzene (17.3 g, 100 mmol) was added over 5 minutes to a solution of lithium diisopropylamide (prepared from the addition of 40 mL of 2.5 N-butyllithium in hexanes to 11.5 g of 0.1 M diisopropylamine at 0° C.) in THF at −70° C. The mixture was stirred cold for 1 hour, after which DMF (8 mL) was added over 10 minutes. The mixture was stirred at −70° C. for an additional 40 minutes, followed by treatment with acetic acid (26 g). The mixture was allowed to warm to ambient temperature and transferred into a mixture of MTBE (200 mL), water (200 mL), and hydrochloric acid (4 N, 150 mL). The layers were partitioned and the organic portion was concentrated under reduced pressure to provide the title compound. MS (DCI/NH3) m/z 202 (M+H)+.

Workup

  1. stirringThe mixture was stirred at −70° C. for an additional 40 minutes
  2. customThe layers were partitioned
  3. concentrationthe organic portion was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce9da09e34014a23b35191568c769192
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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