HCID 86693060, compound → HCID 86693061, compound

HRID 575028Notes

Reaction equation

HRID 575028 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:19])[CH2:11][CH:10]([C:12]([O:14]C(C)(C)C)=[O:13])[CH2:9]2)=[CH:4][C:3]=1[F:20]>CO.[OH-].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:19])[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9]2)=[CH:4][C:3]=1[F:20]

Participants

3

Reactant 1

HCID 86693060HCID 86693060, compound

Product 1

HCID 86693061HCID 86693061, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 23721981Sodium hydroxide methanolSolvent

Procedure

Into a 1000-mL round-bottom flask was placed a solution of tert-butyl 3-(4-bromo-3-fluorophenyl)-3-hydroxycyclobutane-1-carboxylate (62 g, 179.60 mmol, 1.00 equiv) in methanol/NaOH (40%) (300/300 mL). The resulting solution was stirred at room temperature for 3 h, concentrated under vacuum and extracted with 3×200 mL of ethyl acetate. The pH value of the aqueous layer was adjusted to 4 with hydrogen chloride (2 mol/L). The resulting solution was extracted with 3×300 mL of ethyl acetate. The organic layers were combined, washed with 1×500 mL of water and 1×500 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 50 g (96%) of 3-(4-bromo-3-fluorophenyl)-3-hydroxycyclobutane-1-carboxylic acid as a yellow liquid.

Workup

  1. customInto a 1000-mL round-bottom flask was placed
  2. concentrationconcentrated under vacuum
  3. extractionextracted with 3×200 mL of ethyl acetate
  4. extractionThe resulting solution was extracted with 3×300 mL of ethyl acetate
  5. washwashed with 1×500 mL of water and 1×500 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c4b042953416464e8ca3bc61f5435166
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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