Sodium Bicarbonate → HCID 54205761, compound

HRID 442916Notes

Reaction equation

HRID 442916 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]=[CH:14][C:15]([O:22][CH3:23])=[C:16]([S:18](Cl)(=[O:20])=[O:19])[CH:17]=1.C([O-])(O)=O.[Na+]>C(OCC)C>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:22][CH3:23])=[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:19])=[O:20])[CH:17]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5200205-Bromo-2-methoxybenzene-1-sulfonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 54205761HCID 54205761, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.25 g (8.76 mmol) of orcinol monohydrate and 2.50 g (8.76 mmol) of 5-bromo-2-methoxybenzenesulfonyl chloride in 25 mL of diethyl ether was added 25 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 1.92 g (59%) of the desired product as a pale yellow crystalline solid: 1H-NMR (300 MHz; CDCl3) δ 7.93 (d, 1 H, J=2.5 Hz), 7.69 (dd, 1 H, J=8.9, 2.5 Hz), 6.98 (d, 1 H, J=8.9 Hz), 6.54 (br s, 1 H), 6.51 (br s, 1 H), 6.41 (t, 1 H, J=2.2 Hz), 3.98 (s, 3 H) and 2.24 (s, 3 H).

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 1.92 g (59%) of the desired product as a pale yellow crystalline solid

Sources & evidence

ORD record
ord-e59daeba75544cc0a668e5c12e860249
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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