Thionyl Chloride → [3,4-bis(difluoromethoxy)phenyl]-(2-bromo-5-pyridyl) chloromethane

HRID 567953Notes

Reaction equation

HRID 567953 reaction equation
[F:1][CH:2]([F:23])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:16]2[CH:17]=[N:18][C:19]([Br:22])=[CH:20][CH:21]=2)O)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12].O=S(Cl)[Cl:26].C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][CH:2]([F:23])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:16]2[CH:17]=[N:18][C:19]([Br:22])=[CH:20][CH:21]=2)[Cl:26])[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 10971303HCID 10971303, compound

Product 1

HCID 11144147[3,4-bis(difluoromethoxy)phenyl]-(2-bromo-5-pyridyl) chloromethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution [3,4-Bis(difluoromethoxy)phenyl]-(6-bromo-3-pyridyl)methanol (15.8 g,40.0 mmol) in 400 mL of CH2Cl2, was added 3.8 mL (52.0 nimol) of SOCl2. The solution was stirred 45 minutes at room temperature and poured into a saturated aqueous solution of NaHCO3. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were dry over MgSO4 and concentrated under reduced pressure. The crude chloride was used directly for the next step without any purification.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2
  2. dry with materialthe combined organic layers were dry over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude chloride was used directly for the next step without any purification

Sources & evidence

ORD record
ord-3bab9832e953440686340ca9eaff7b20
Source dataset
uspto-grants-2001_01
Patent number
US06180650B2

Reaction notes

Loading…