1-(4-Bromophenyl)cyclobutane-1-carboxylic acid → (1-(4-Bromophenyl)cyclobutyl)methanol

HRID 1054739Notes

Reaction equation

HRID 1054739 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](O)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 167699191-(4-Bromophenyl)cyclobutane-1-carboxylic acid

Product 1

HCID 58538689(1-(4-Bromophenyl)cyclobutyl)methanolYield 62%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(4-bromophenyl)cyclobutanecarboxylic acid (300 mg, 1.20 mmol) in 1,4-dioxane (5 mL) was added borane dimethylsulfide complex (0.24 mL, 2.4 mmol) dropwise at 0° C. The ice bath was removed, and the reaction mixture was stirred at room temperature for 10 min. The reaction mixture was quenched with methanol (20 mL). The organic solvents were removed under reduced pressure to give a residue, which was dissolved in ethyl acetate, then washed with brine. The organic phase was concentrated to give [1-(4-bromophenyl)cyclobutyl]methanol (170 mg, 62% yield) as a yellow oil which was used directly in the next step.

Workup

  1. customThe ice bath was removed
  2. customThe reaction mixture was quenched with methanol (20 mL)
  3. customThe organic solvents were removed under reduced pressure
  4. customto give a residue, which
  5. washwashed with brine
  6. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-a43ab158e3014363b8dc7631e25448f1
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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