Toluene → 3-(4-Fluorophenyl)propionyl chloride

HRID 1592357Notes

Reaction equation

HRID 1592357 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O.C1(C)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([Cl:15])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 1363023-(4-Fluorophenyl)propionic acid

Product 1

HCID 219642583-(4-Fluorophenyl)propionyl chlorideYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(para-Fluorophenyl)propionic acid (25.00 g, 150.0 mmol, 1 eq.) was dissolved in methylene chloride (100 mL) at 25° C. under N2 and thionyl chloride (54.2 mL, 740.0 mmol, 5 eq.) added dropwise via an addition funnel. Worked up after 24 hours by stripping off the solvent then rerotovaping 2 times from toluene (25 mL) to obtain 24.3 g of a yellow oil.

Sources & evidence

ORD record
ord-85272490bfd14b97a424579e5dc9d4dc
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

Loading…