Methanol → Methyl 4-bromo-3-fluorobenzeneacetate

HRID 425329Notes

Reaction equation

HRID 425329 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#N)=[CH:4][C:3]=1[F:11].S(=O)(=O)(O)O.[OH2:17].[CH3:18][OH:19]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:19][CH3:18])=[O:17])=[CH:4][C:3]=1[F:11]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 116009532-(4-Bromo-3-fluorophenyl)acetonitrile

Product 1

HCID 71265948Methyl 4-bromo-3-fluorobenzeneacetate

Procedure

(4-bromo-3-fluorophenyl)acetonitrile (40 g, 0.18 mol) was dissolved in 120 mL methanol, and 65 mL concentrated sulfuric acid were added. After heating at reflux overnight, the reaction mixture was cooled, and poured into 600 mL water, and the product was extracted with CH2Cl2. The combined extracts were washed with 10% sodium carbonate solution, dried, and concentrated to afford methyl (4-bromo-3-fluorophenyl)acetate.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux overnight
  3. temperaturethe reaction mixture was cooled
  4. extractionthe product was extracted with CH2Cl2
  5. washThe combined extracts were washed with 10% sodium carbonate solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c486df2e7ae841448520cfd8662d0b6a
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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