Thionyl Chloride → 4-[(4-Fluorophenyl)methoxy]benzene-1-sulfonyl chloride

HRID 1359040Notes

Reaction equation

HRID 1359040 reaction equation
[Na+].[F:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([O-])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:23])=O>CN(C)C=O>[F:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([Cl:23])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23701365Sodium 4-(4-fluorobenzyloxy)benzenesulfonate

Product 1

HCID 181794244-[(4-Fluorophenyl)methoxy]benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To a stirred solution of 4-hydroxybenzenesulfonic acid sodium salt dihydrate (5.13 g, 22.1 mmol) in 23 mL of 1 N sodium hydroxide was added a solution of 4-fluorobenzyl bromide (3.3 mL, 26.5 mmol) in 20 mL of ethanol. The mixture was heated at reflux for two days, then cooled to ambient temperature (22° C.), whereupon a white precipitate formed. The flaky white solids were collected by filtration, rinsed with ethyl acetate and diethyl ether, and dried to give 4.95 g of 4-(4-fluoro-benzyloxy)-benzenesulfonic acid sodium salt. A stirred solution of 4-(4-fluoro-benzyloxy)-benzenesulfonic acid sodium salt (13.0 g, 42.7 mmol) in 50 mL of thionyl chloride and two drops of dimethylformamide was heated at a gentle reflux for 8 hours. The mixture was concentrated to a yellow solid which was suspended in ethyl acetate and filtered. The filtrate was concentrated to 11.2 g of 4-(4-fluorobenzyloxy)benzenesulfonyl chloride as a light yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.95-7.98 (m, 2 H), 7.38-7.41 (m, 2 H), 7.06-7.12 (m, 4 H), 5.12 (s, 2 H).

Workup

  1. temperaturea gentle reflux for 8 hours
  2. concentrationThe mixture was concentrated to a yellow solid which
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to 11.2 g of 4-(4-fluorobenzyloxy)benzenesulfonyl chloride as a light yellow solid

Sources & evidence

ORD record
ord-626e54a3d4d14b7ab51f8224d686d339
Source dataset
uspto-grants-2003_07
Patent number
US06599890B1

Reaction notes

Loading…