Acetic Acid → 4-(2-Bromoethoxy)-3-fluorobenzoic acid

HRID 626228Notes

Reaction equation

HRID 626228 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8](C#N)=[CH:7][C:6]=1[F:13].[C:14](=[O:17])(O)[O-:15].[Na+].C(O)(=O)C>O.S(=O)(=O)(O)O>[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C:14]([OH:15])=[O:17])=[CH:7][C:6]=1[F:13]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 159788884-(2-Bromoethoxy)-3-fluorobenzonitrile

Product 1

HCID 896557994-(2-Bromoethoxy)-3-fluorobenzoic acidYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

4-(2-Bromoethoxy)-3-fluorobenzonitrile (3.78 g, 15.5 mmol) in water (18 mL) and concentrated sulfuric acid (18 mL) was heated at 110° C. for 12 hours. The solution was then cooled to room temperature and neutralized with solid sodium bicarbonate. Acidification with glacial acetic acid gave a white solid precipitate, which was collected by filtration and dissolved in dichloromethane. The resultant solution was dried over sodium sulfate. The dichloromethane solution was then filtered and evaporated to give the product as a beige-colored solid (2.65 g, 65%). 1H NMR (400 MHz, DMSO-d6) δ 13.00 (brs, 1H), 7.44 (d, J=8.4 Hz, 1H), 7.69 (d, J=12.0 Hz, 1H), 7.29 (dd, J=8.8 Hz, 8.4 Hz, 1H), 4.48 (t, J=5.2 Hz, 2H), 3.85 (t, J=5.2 Hz, 2H).

Workup

  1. filtrationwas collected by filtration
  2. dissolutiondissolved in dichloromethane
  3. dry with materialThe resultant solution was dried over sodium sulfate
  4. filtrationThe dichloromethane solution was then filtered
  5. customevaporated

Sources & evidence

ORD record
ord-3dd294b7f52948788c24033b787d370a
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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