5-Bromo-2-methoxy-4-methylbenzenesulfonic acid dihydrate → HCID 13012786, compound

HRID 322095Notes

Reaction equation

HRID 322095 reaction equation
O.O.Br[C:4]1[C:5]([CH3:16])=[CH:6][C:7]([O:14][CH3:15])=[C:8]([S:10]([OH:13])(=[O:12])=[O:11])[CH:9]=1>CO.[Pd]>[CH3:15][O:14][C:7]1[CH:6]=[C:5]([CH3:16])[CH:4]=[CH:9][C:8]=1[S:10]([OH:13])(=[O:12])=[O:11]

Participants

4

Reactant 1

HCID 882196925-Bromo-2-methoxy-4-methylbenzenesulfonic acid dihydrate

Product 1

HCID 13012786HCID 13012786, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 5-bromo-2-methoxy-4-methylbenzenesulfonic acid dihydrate (from (a), 125 g, 0.394 moles) in methanol (1.25 liters, 10 ml/g) was added 5% Palladium on carbon catalyst (12.5 g, 0.1 g/g) and the suspension was hydrogenated at 60° C. and 414 kPa (60 psi) for 16 hours. The reaction mixture was filtered over celite and concentrated to dryness. The crude product was slurried in dichloromethane (250 ml), cooled to 0-5° C. and the subtitle compound (67.5 g, 75% yield) isolated in two crops as a white crystalline solid

Workup

  1. customwas hydrogenated at 60° C.
  2. filtrationThe reaction mixture was filtered over celite and
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e3180311530f488fac73f07330603240
Source dataset
uspto-grants-2001_04
Patent number
US06211223B1

Reaction notes

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