Sodium Bicarbonate → HCID 54410095, compound

HRID 442973Notes

Reaction equation

HRID 442973 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]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1.C([O-])(O)=O.[Na+]>C(OCC)C>[F:11][C:12]1[CH:13]=[C:14]([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:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 54410095HCID 54410095, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 0.704 g (5.67 mmol) of orcinol monohydrate and 1.00 g (5.15 mmol) of 3-fluorobenzenesulfonyl chloride in 25 mL of diethyl ether was added 25 mL of saturated aqueous NaHCO3 and the biphasic mixture was 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 1.41 g of a pale amber-colored oil. This material was flash chromatographed on 65 g of silica gel with 3% ethyl acetate-dichloromethane to afford 935 mg (68%) of the desired product as a colorless syrup: 1H-NMR (300 MHz; CDCl3) δ 7.66 (ddd, 1H, J=7.8, 1.7, 1.1 Hz), 7.55 (m, 2H), 7.38 (tdd, 1H, J=8.3, 2.6, 1.1 Hz), 6.56 (m, 1H), 6.40 (m, 1H), 6.33 (td, 1H, J=2.2, 0.5 Hz), 5.29 (s, 1H) and 2.23 (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 to 1.41 g of a pale amber-colored oil
  6. customchromatographed on 65 g of silica gel with 3% ethyl acetate-dichloromethane

Sources & evidence

ORD record
ord-68cba2126ace4ed4939b918c0b72d52d
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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