Hydrochloric Acid → HCID 65203823, compound

HRID 575020Notes

Reaction equation

HRID 575020 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])=[CH:4][C:3]=1[F:17].[Li+].[OH-].O1CCCC1.Cl>O>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[F:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86693053Butanoic acid, 4-(4-bromo-3-fluorophenoxy)-, ethyl ester

Product 1

HCID 65203823HCID 65203823, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Into a 2000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of argon was placed ethyl 4-(4-bromo-3-fluorophenoxy)butanoate (80.6 g, 264.14 mmol, 1.00 equiv), LiOH (12.7 g, 530.27 mmol, 2.00 equiv), tetrahydrofuran (250 mL), and water (240 mL). The resulting solution was stirred at 50° C. overnight, cooled to 0° C. with a water/ice bath, adjusted to pH=3-4 with hydrochloric acid (2 N) and extracted with 3×100 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was triturated in 30 mL of EA to afford 50 g (68%) of 4-(4-bromo-3-fluorophenoxy)butanoic acid as a white solid.

Workup

  1. customInto a 2000-mL 4-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of argon
  3. temperaturecooled to 0° C. with a water/ice bath
  4. extractionextracted with 3×100 mL of ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was triturated in 30 mL of EA

Sources & evidence

ORD record
ord-fe639f44afe940c1a6ad0e2471a5f44a
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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