Ethyl Acetate → 2-Bromo-4-fluorobenzaldehyde

HRID 857334Notes

Reaction equation

HRID 857334 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9]Br.O.C[N+]1([O-])CC[O:16]CC1.[NH4+].[Cl-].CCOC(C)=O>O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[O:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 107069772-Bromo-1-(bromomethyl)-4-fluorobenzene

Product 1

HCID 27733192-Bromo-4-fluorobenzaldehydeYield 98.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the benzyl bromide of Step 1 (59 g, 220 mmol) in dioxane (500 mL) at r.t. was added N-methylmorpholine N-oxide monohydrate (89 g, 660 mmol). The reaction mixture was stirred for 1 hour at 70° C. and poured into a mixture of saturated aqueous NH4Cl and EtOAc. The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, dried over Na2SO4 and concentrated to give 44 g of the title compound as a white solid and used as such.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6ec8e74b329d4168af8ab1e906afc5a9
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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