Sodium Hydroxide → HCID 19013860, compound

HRID 1728513Notes

Reaction equation

HRID 1728513 reaction equation
[OH-:1].[Na+].BrBr.[F:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])C)=[CH:11][CH:10]=1>O.O1CCOCC1>[F:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([OH:17])=[O:1])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 19013861HCID 19013861, compound

Product 1

HCID 19013860HCID 19013860, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 11.3 g of sodium hydroxide in 75 ml of water was charged in a 300 ml-three necked flask and cooled to 0° C., and 12.3 g of bromine was added thereto in 15 minutes under stirring, followed by addition of 30 ml of dioxane. The resultant mixture solution was added dropwise in 40 minutes to a solution which was obtained by dissolving 5.2 g of p-(2-fluorodecyloxy) acetophenone in 170 ml of dioxane followed by addition of 10 ml of water, and subjected to reaction for 3.5 hours while being kept below 10° C. Thereafter, the excessive hypobromite was removed by addition of a hydrosulfite aqueous solution, followed by acidification with addition of 6N-hydrochloric acid aqueous solution, and addition of 500 ml of water to precipitate a crystal, which was then recovered by filtration. The crystal was recrystallized from isopropyl ether to obtain 4.1 g of p-(2-fluorodecyloxy)benzoic acid.

Workup

  1. customwas obtained
  2. customsubjected to reaction for 3.5 hours
  3. customwhile being kept below 10° C
  4. customThereafter, the excessive hypobromite was removed by addition of a hydrosulfite aqueous solution
  5. additionfollowed by acidification with addition of 6N-hydrochloric acid aqueous solution, and addition of 500 ml of water
  6. customto precipitate a crystal, which
  7. filtrationwas then recovered by filtration
  8. customThe crystal was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-08fd45a5ac624a48b5f3b859c5de29de
Source dataset
uspto-grants-1994_07
Patent number
US05328639

Reaction notes

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