Water → 2'-(2,4,6-Trimethoxybenzylthio)biphenyl-3-ol

HRID 2097697Notes

Reaction equation

HRID 2097697 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][CH2:16][C:17]2[C:22]([O:23][CH3:24])=[CH:21][C:20]([O:25][CH3:26])=[CH:19][C:18]=2[O:27][CH3:28])O1.[OH2:30]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:24][O:23][C:22]1[CH:21]=[C:20]([O:25][CH3:26])[CH:19]=[C:18]([O:27][CH3:28])[C:17]=1[CH2:16][S:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:30])[CH:10]=1

Participants

5

Reactant 2

HCID 962WaterHCID 686554014,4,5,5-Tetramethyl-2-(2-(2,4,6-trimethoxybenzylthio)phenyl)-1,3,2-dioxaborolane

Product 1

HCID 668706052'-(2,4,6-Trimethoxybenzylthio)biphenyl-3-ol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4,4,5,5-tetramethyl-2-(2-(2,4,6-trimethoxybenzylthio)phenyl)-1,3,2-dioxaborolane (1.2 g, 2.9 mmol), 3-lodophenol (0.65 g, 2.9 mmol), Ag2CO3 (0.82 g, 2.9 mmol) and Pd(PPh3)4 (0.16 g, 0.15 mmol) in 6 ml of THF was refluxed in the dark for 12 h. The reaction mixture was poured into H2O and the resulting mixture extracted with ether. The organic layer was washed with brine (3×20 ml) and dried over MgSO4 and concentrated. The residue was purified by silica flash chromatography (40/60, ethylacetate/hexane) to afford 2′-(2,4,6-trimethoxybenzylthio)biphenyl-3-ol.

Workup

  1. temperaturewas refluxed in the dark for 12 h
  2. extractionthe resulting mixture extracted with ether
  3. washThe organic layer was washed with brine (3×20 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica flash chromatography (40/60, ethylacetate/hexane)

Sources & evidence

ORD record
ord-9e62347fa23a464189f336d35916b84d
Source dataset
uspto-grants-2013_05
Patent number
US08450374B2

Reaction notes

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