Hydrochloric Acid → HCID 18677872, compound

HRID 1634275Notes

Reaction equation

HRID 1634275 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[C:12]1(B(O)O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.Cl>CS(C)=O>[C:20]1([S:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[C:21]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2545321-Naphthaleneboronic acidHCID 6913934HCID 6913934, compound

Product 1

HCID 18677872HCID 18677872, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 344 mg (2.0 mmol) 4-methoxybenzene sulfinic acid, 688 mg (4.0 mmol) 1-naphthyl boronic acid, 1.39 mL (10.0 mmol) triethylamine, 363 mg (2.0 mmol) cupric acetate, 350 mg 4A molecular sieves, and 10 mL dry dimethylsulfoxide was stirred under a stream of air for 36 hours. The mixture was then poured into dilute aqueous hydrochloric acid, extracted into ethyl acetate, and the organic layer washed with water, aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using ethyl acetate/hexane as eluant to afford 240 mg (40%) of 4-(1-napthylsulfonyl)phenol as an oil.

Workup

  1. extractionextracted into ethyl acetate
  2. washthe organic layer washed with water, aqueous sodium bicarbonate solution, and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-160f98263e9b4b88b6557793557cf47d
Source dataset
uspto-grants-2003_01
Patent number
US06506780B2

Reaction notes

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