4-Fluorobenzyl bromide → Sodium 4-(4-fluorobenzyloxy)benzenesulfonate

HRID 1359039Notes

Reaction equation

HRID 1359039 reaction equation
O.O.[Na+:3].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([O-:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1>[OH-].[Na+].C(O)C>[Na+:3].[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][O:4][C:5]2[CH:10]=[CH:9][C:8]([S:11]([O-:14])(=[O:12])=[O:13])=[CH:7][CH:6]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 23666329Sodium P-phenolsulfonate dihydrate

Product 1

HCID 23701365Sodium 4-(4-fluorobenzyloxy)benzenesulfonateYield 73.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
22 °C

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. temperatureThe mixture was heated
  2. temperatureat reflux for two days
  3. customwhereupon a white precipitate formed
  4. filtrationThe flaky white solids were collected by filtration
  5. washrinsed with ethyl acetate and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-4ca7c8f27a404cb5a805c7bd0b8709ce
Source dataset
uspto-grants-2003_07
Patent number
US06599890B1

Reaction notes

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