Sodium Hydroxide → 2-Chloro-4-fluoro-3-methylbenzoic acid

HRID 1889022Notes

Reaction equation

HRID 1889022 reaction equation
BrBr.[OH-:3].[Na+].[Cl:5][C:6]1[C:11]([CH3:12])=[C:10]([F:13])[CH:9]=[CH:8][C:7]=1[C:14](=[O:16])C>O.O1CCOCC1>[Cl:5][C:6]1[C:11]([CH3:12])=[C:10]([F:13])[CH:9]=[CH:8][C:7]=1[C:14]([OH:16])=[O:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 10583732HCID 10583732, compound

Product 1

HCID 108453152-Chloro-4-fluoro-3-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

Bromine (7.61 mL, 148 mmol) was added dropwise to sodium hydroxide (19.70 g, 492 mmol) dissolved in Water (80 mL) maintaining temperature<10° C. 1-(2-chloro-4-fluoro-3-methylphenyl)ethanone (I73) (9.19 g, 49.2 mmol) dissolved in 1,4-dioxane (80 mL) was added dropwise at 0° C. and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with chloroform (2×20 mL) and the aqueous phase acidified to pH1 with concentrated hydrochloric acid. The resulting precipitate was filtered, washed with water, a little diethyl ether (Note: product has some ether solubility) and dried to afford product in 8.89 g. This was recrystalised from toluene to afford product in 6.25 g as fine white needles.

Workup

  1. additionwas added dropwise at 0° C.
  2. washThe reaction mixture was washed with chloroform (2×20 mL)
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried
  6. customto afford product in 8.89 g
  7. customThis was recrystalised from toluene
  8. customto afford product in 6.25 g as fine white needles

Sources & evidence

ORD record
ord-5b777416e0404e7983dce30623674868
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

Loading…