Trifluoroacetic acid → Methyl 3-(4-bromophenyl)cyclobutane-1-carboxylate

HRID 575029Notes

Reaction equation

HRID 575029 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(O)[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16]2)=[CH:11][CH:10]=1.[SiH](CC)(CC)CC>>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH2:16][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:18]2)=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 53418816Methyl 3-(4-bromophenyl)-3-hydroxycyclobutane-1-carboxylate

Product 1

HCID 53418991Methyl 3-(4-bromophenyl)cyclobutane-1-carboxylateYield 98.9%

Conditions

Temperature
17.5 °C

Procedure

Into a 20-L 4-necked round-bottom flask was placed trifluoroacetic acid (12 L), methyl 3-(4-bromophenyl)-3-hydroxycyclobutane-1-carboxylate (2330 g, 8.17 mol, 1.00 equiv), followed by the addition of Et3SiH (3556 g, 30.58 mol, 5.00 equiv) dropwise with stirring at 10-25° C. The resulting solution was stirred at room temperature for 0.5 h, concentrated under vacuum, diluted with 8 L of H2O and extracted with 1×8 L of ethyl acetate. The organic layers were combined, washed with 1×3 L of saturated aqueous sodium bicarbonate and 1×2 L of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 2175 g (crude) of methyl 3-(4-bromophenyl)cyclobutane-1-carboxylate as an orange oil.

Workup

  1. customInto a 20-L 4-necked round-bottom flask was placed
  2. stirringThe resulting solution was stirred at room temperature for 0.5 h
  3. concentrationconcentrated under vacuum
  4. additiondiluted with 8 L of H2O
  5. extractionextracted with 1×8 L of ethyl acetate
  6. washwashed with 1×3 L of saturated aqueous sodium bicarbonate and 1×2 L of brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cad3cc8d8b664a5d8fead3d27d6adc99
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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