Water → alpha-(2,3-Dichloro-4-methoxyphenyl)-2-pyridinemethanol

HRID 568641

Reaction equation

HRID 568641 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[Cl:13][C:14]1[C:21]([Cl:22])=[C:20]([O:23][CH3:24])[CH:19]=[CH:18][C:15]=1[CH:16]=[O:17].O>C1COCC1>[Cl:13][C:14]1[C:21]([Cl:22])=[C:20]([O:23][CH3:24])[CH:19]=[CH:18][C:15]=1[CH:16]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[OH:17]

Participants

6

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 130156892,3-Dichloro-4-methoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 13015690alpha-(2,3-Dichloro-4-methoxyphenyl)-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-65 °C

Procedure

29.3 g of 2-bromopyridine in 150 ml of dry THF is added to 75 ml of 2.6M n-butyllithium that was chilled to -65° C. 2,3-dichloro-4-methoxybenzaldehyde (38.0 g) is then added in 300 ml of THF and the reaction mixture allowed to come to room temperature. It is poured into H2O and the crystalline product filtered off, washed with ether and dried to give α-(2,3-dichloro-4-methoxyphenyl)-2-pyridinemethanol, mp 174°-176° C.

Workup

  1. customto come to room temperature
  2. filtrationthe crystalline product filtered off
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-386848d5c489420ea7ebd52b0c9b35f7
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Linked notes

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