1-Bromo-2,2-dimethylpropane → 1-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)-3,3-dimethylbutan-1-ol

HRID 1049585Notes

Reaction equation

HRID 1049585 reaction equation
[Mg].Br[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].[F:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[C:17]1[C:18]([CH:33]=[O:34])=[CH:19][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:21][CH:22]=1.[Cl-].[NH4+]>C(OCC)C>[F:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:19][C:18]=1[CH:33]([OH:34])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 124151-Bromo-2,2-dimethylpropaneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 1177599142'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-carbaldehyde

Product 1

HCID 1177597911-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)-3,3-dimethylbutan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of magnesium (133 mg) and diethyl ether (10 mL) was added 1-bromo-2,2-dimethylpropane (0.68 mL), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added a solution of 2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-carbaldehyde (1.02 g) in diethyl ether (5 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (674 mg) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f30c0d293c794754b762970980d7cc28
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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