m-Bromobenzenesulphonyl chloride → HCID 54559609, compound

HRID 442979Notes

Reaction equation

HRID 442979 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[Br: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>[Br: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 17943m-Bromobenzenesulphonyl chlorideHCID 516892Sodium BicarbonateHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 54559609HCID 54559609, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 534 mg (4.30 mmol) of orcinol monohydrate and 1.00 g (3.91 mmol) of 3-bromobenzenesulfonyl 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 1.4 g of an amber-colored resin. Chromatography on 65 g of silica gel with 3% ethyl acetate-dichloromethane afforded 870 mg (65%) of the desired product as a colorless syrup: 1H-NMR (300 MHz; CDCl3) δ 8.02 (t, 1H, J=1.8 Hz), 7.79 (m, 2H), 7.41 (t, 1H, J=7.9 Hz), 6.57 (m, 1H), 6.40 (m, 1H), 6.33 (t, 1H, J=2.2 Hz) and 2.24 (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 1.4 g of an amber-colored resin

Sources & evidence

ORD record
ord-bede1dc5c55a4200afb34e467cb481dc
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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