Methanol → Methyl 4-bromo-3-fluorobenzeneacetate

HRID 1881407Notes

Reaction equation

HRID 1881407 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-1f802d86fc1f404a85dc2c82c04d1206
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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