Borane;tetrahydrofuran → [1-(4-Bromo-2-methoxyphenyl)cyclobutyl]methanol

HRID 1054852Notes

Reaction equation

HRID 1054852 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)=[C:4]([O:15][CH3:16])[CH:3]=1.B.O1CCCC1>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][OH:13])[CH2:9][CH2:10][CH2:11]2)=[C:4]([O:15][CH3:16])[CH:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 866988401-(4-Bromo-2-methoxyphenyl)cyclobutanecarboxylic acid

Product 1

HCID 86698841[1-(4-Bromo-2-methoxyphenyl)cyclobutyl]methanolYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(4-bromo-2-methoxyphenyl)cyclobutanecarboxylic acid (320 mg, 1.12 mmol) in dry tetrahydrofuran (10 mL) was added borane-tetrahydrofuran (0.67 mL, 6.7 mmol) dropwise. The mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched by water and extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, and concentrated to give the title compound (280 mg, 92%) as a colorless oil. 1H NMR (500 MHz, DMSO-d6) δ 7.05 (m, 2H), 6.86 (d, 1H), 4.57 (t, 1H), 3.73 (s, 3H), 3.55 (d, 2H), 2.05-2.17 (m, 4H), 1.95 (m, 1H), 1.69 (m, 1H).

Workup

  1. customThe reaction mixture was quenched by water
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8b297a8f691e4aedb4995a0b3744692e
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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