Ethanol → 4-Benzyloxy-2-fluoro-phenyl acetic acid

HRID 898662Notes

Reaction equation

HRID 898662 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[C:11]([F:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[OH-:21].[K+].[CH2:23]([OH:25])C>O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][C:23]([OH:25])=[O:21])=[C:11]([F:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 14797Potassium HydroxideHCID 158958914-(Benzyloxy)-1-(bromomethyl)-2-fluorobenzene2×

Product 1

HCID 121369924-Benzyloxy-2-fluoro-phenyl acetic acidYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-benzyloxy-2-fluoro-benzyl bromide (Compound 10, 18 g, 58 mmol) in a mixture of ethanol (90 mL) and water (10 mL) was treated with sodium cyanide (4.25 g, 86,8 mmol) and the resulting reaction mixture was heated at 70° C. for 1 h. Potassium hydroxide (6.5 g, 115.7 mmol) was then added and heating was continued for another 5 h. The volatiles were evaporated in vacuo, the residue was diluted with water and neutralized with hydrochloric acid and the precipitated solid was filtered, washed with water and dried to afford the title product as a yellow solid (13 g, 81%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureheating
  3. customThe volatiles were evaporated in vacuo
  4. additionthe residue was diluted with water and neutralized with hydrochloric acid
  5. filtrationthe precipitated solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-c0dafd751dd242a89018cb125bdff63b
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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