5-Fluoro-2-methylbenzenesulphonyl chloride → HCID 54447329, compound

HRID 442952Notes

Reaction equation

HRID 442952 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:22])=[C:16]([S:18](Cl)(=[O:20])=[O:19])[CH:17]=1.C([O-])(O)=O.[Na+]>C(OCC)C>[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:22])=[C:16]([S:18]([O:5][C:4]2[CH:3]=[C:2]([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=2)(=[O:20])=[O:19])[CH:17]=1

Participants

5

Reactant 3

HCID 1362865-Fluoro-2-methylbenzenesulphonyl chlorideHCID 516892Sodium BicarbonateHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 54447329HCID 54447329, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.00 g (8.05 mmol) of orcinol monohydrate and 1.63 g (7.38 mmol) of 5-fluoro-2-methylbenzenesulfonyl chloride in 20 mL of diethyl ether was added 20 mL of saturated aqueous NaHCO3 and the biphasic mixture stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2×30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2SO4) and concentrated to give 2.2 g of an orange syrup. Crystallization from dichloromethane-hexane (two crops) afforded 1.24 g (54%) of the title compound as a light orange powder: 1H-NMR (300 MHz; CDCl3) δ 7.57 (dd, 1H, J=8.2, 2.8 Hz), 7.36 (dd, 1H, J=8.6, 5.2 Hz), 7.22 (td, 1H, J=8.4, 2.8 Hz), 6.52 (m, 1H), 6.39 (m, 1H), 6.30 (t, 1H, J=2.2 Hz), 2.69 (s, 3H) and 2.21 (s, 3H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with 2×30 mL of ethyl acetate
  3. washThe combined organic layers were washed with 50 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-63a0df9a12e9438daebbb47312c29638
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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