Dimethylformamide → (2-Bromo-5-difluoromethoxy-4-methoxy-phenyl)-acetic acid chloride

HRID 1691786Notes

Reaction equation

HRID 1691786 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH:11]([F:13])[F:12])=[CH:4][C:3]=1[CH2:14][C:15]([OH:17])=O.C(Cl)(=O)C([Cl:21])=O.CN(C=O)C>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH:11]([F:13])[F:12])=[CH:4][C:3]=1[CH2:14][C:15]([Cl:21])=[O:17]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 59377691(2-Bromo-5-difluoromethoxy-4-methoxy-phenyl)-acetic acid

Product 1

HCID 59377702(2-Bromo-5-difluoromethoxy-4-methoxy-phenyl)-acetic acid chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Bromo-5-difluoromethoxy-4-methoxy-phenyl)-acetic acid (350 mg, 1.12 mmol) was dissolved in 6 ml dichloromethane and 0.1 ml oxalyl chloride and 0.01 ml DMF was added. The solution was stirred at room temperature until gas evolution stopped, then concentrated under reduced pressure. Dichloromethane (6 ml) was added to the residue and the solvent removed again to assure that all the oxalyl chloride was removed giving 118 mg of crude (2-bromo-5-difluoromethoxy-4-methoxy-phenyl)-acetic acid chloride.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionDichloromethane (6 ml) was added to the residue
  3. customthe solvent removed again
  4. customwas removed

Sources & evidence

ORD record
ord-0b73919b5932465795173c18c2efa66c
Source dataset
uspto-grants-2012_04
Patent number
US08153808B2

Reaction notes

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