Toluene → 3,5-Difluoro-4-(2-propynyloxy)benzoyl chloride

HRID 602028

Reaction equation

HRID 602028 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([F:22])[C:17]=1[O:18][CH2:19][C:20]#[CH:21])[C:12](O)=[O:13].S(Cl)([Cl:25])=O>CN(C=O)C>[F:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([F:22])[C:17]=1[O:18][CH2:19][C:20]#[CH:21])[C:12]([Cl:25])=[O:13]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 574456663,5-Difluoro-4-(2-propynyloxy)benzoic acid

Product 1

HCID 574456963,5-Difluoro-4-(2-propynyloxy)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 17 ml of toluene were added 1.8 g of 3,5-difluoro-4-(2-propynyloxy)benzoic acid, 1 ml of thionyl chloride and 10 mg of DMF and the mixture was heated under reflux for 4 hours. Then, the reaction mixture was concentrated under reduced pressure to obtain 1.9 g of 3,5-difluoro-4-(2-propynyloxy)benzoyl chloride represented by the formula:

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. concentrationThen, the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d638ee2f8f2f4de88ea2035df800bcc1
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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