Hydrochloric Acid → HCID 13191806, compound

HRID 1731301Notes

Reaction equation

HRID 1731301 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C([Li])CCC.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.Cl>CCOCC>[Br:8][C:4]1[N:3]=[C:2]([CH:19]([OH:20])[C:18]2[CH:21]=[CH:22][C:15]([Cl:14])=[CH:16][CH:17]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 122742,6-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 13191806HCID 13191806, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 2,6-dibromopyridine (100 g) in dry ether (1 l) under nitrogen at -70° was added dropwise during 2 hr a solution of n-butyllithium (270 mL, 1.7M in hexane). After an additional 0.5 hr, a solution of p-chlorobenzaldehyde (65 g) in dry ether (500 mL) was added during a 1 hr period. The reaction mixture was allowed to warm to ca. 0° and then poured into aqueous hydrochloric acid (1 l, 4N). The ether layer was separated and the aqueous layer was extracted with two additional portions (300 mL) of ether. The combined ether layers were washed with water (500 mL), dried (Na2SO4) and concentrated to give a syrup. The crude product was chromatographed on silica gel using the Waters Prep 500 (trademark of Waters Associates Inc., Milford, MA 01757) with methylene chloride to provide α-(6-bromo-2-pyridyl)-4-chlorobenzyl alcohol (93.8 g), m.p. 64.5°-65°.

Workup

  1. temperatureto warm to ca. 0°
  2. customThe ether layer was separated
  3. extractionthe aqueous layer was extracted with two additional portions (300 mL) of ether
  4. washThe combined ether layers were washed with water (500 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a syrup
  8. customThe crude product was chromatographed on silica gel using the Waters Prep 500 (trademark of Waters Associates Inc., Milford, MA 01757) with methylene chloride

Sources & evidence

ORD record
ord-2851be3e179947bc9beba66ea47fe85a
Source dataset
uspto-grants-1986_11
Patent number
US04621094

Reaction notes

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