Ammonium Chloride → 1-(2-Fluoro-6-methoxyphenyl)ethanol

HRID 578774Notes

Reaction equation

HRID 578774 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5].[CH3:12][Li].[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]([OH:5])[CH3:12]

Participants

5

Procedure

To a solution of 2-fluoro-6-methoxybenzaldehyde (0.5 g) in tetrahydrofuran (10 mL) was added methyllithium (1.15 mol/L diethyl ether solution, 3.4 mL) at −78° C., and the mixture was stirred at the same temperature for 1 hour. Then the mixture was stirred at room temperature for 30minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (0.45 g).

Workup

  1. stirringThen the mixture was stirred at room temperature for 30minutes
  2. extractionthe resulting mixture was extracted with diethyl ether
  3. washThe extract was washed with water and brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f6a85eabb8784281baff17c71f46ed91
Source dataset
uspto-grants-2015_05
Patent number
US09040693B2

Reaction notes

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