2-(4-Bromo-3,5-dimethylphenoxy)-2-methylpropanoic acid → 2-(4-Bromo-3,5-dimethyl-phenoxy)-2-methyl-propan-1-ol

HRID 237505Notes

Reaction equation

HRID 237505 reaction equation
[Br:1][C:2]1[C:14]([CH3:15])=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8](O)=[O:9])=[CH:4][C:3]=1[CH3:16].O.Cl>O1CCCC1>[Br:1][C:2]1[C:14]([CH3:15])=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[CH2:8][OH:9])=[CH:4][C:3]=1[CH3:16]

Participants

4

Reactant 2

HCID 209902642-(4-Bromo-3,5-dimethylphenoxy)-2-methylpropanoic acidHCID 21885828Hydrate;hydrochloride

Product 1

HCID 866971662-(4-Bromo-3,5-dimethyl-phenoxy)-2-methyl-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Bromo-3,5-dimethyl-phenoxy)-2-methyl-propionic acid (4.45 g) is dissolved in 50 mL of tetrahydrofurane, borane methylsulfide complex (2.6 mL) is added and the reaction mixture is stirred at room temperature for 5 h. The reaction mixture is cooled to 0° C., 10% HCl water solution is added dropwise and the reaction mixture is extracted with dichloromethane. The organic phase is separated, dried over sodium sulfate and concentrated under vacuum. The residue is chromatographed on silica gel (hexane/ethyl acetate 100:0→50:50) to give the title compound. Yield: 2.6 g.

Workup

  1. additionborane methylsulfide complex (2.6 mL) is added
  2. temperatureThe reaction mixture is cooled to 0° C.
  3. extractionthe reaction mixture is extracted with dichloromethane
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue is chromatographed on silica gel (hexane/ethyl acetate 100:0→50:50)

Sources & evidence

ORD record
ord-cab01b67a4ce45559877d2585120974d
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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