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

HRID 652873Notes

Reaction equation

HRID 652873 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-e18c891711e349d7ba5be4862e39b7f1
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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