Sodium Bicarbonate → 4-(2-Bromoethoxy)-3-fluorobenzoic acid

HRID 626132Notes

Reaction equation

HRID 626132 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+]>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

5

Reactant 2

HCID 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 leads to a white solid precipitate, which was collected by filtration and dissolved in dichloromethane. The resulting solution was dried over anhydrous sodium sulfate, filtered, and concentrated to give the product as a beige-colored solid (2.65 g, 65% yield). 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. filtrationAcidification with glacial acetic acid leads to a white solid precipitate, which was collected by filtration
  2. dissolutiondissolved in dichloromethane
  3. dry with materialThe resulting solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-304ab22f27f44ba9acc9ed5f8df32c16
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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