Dichloromethane → 2'-Mercaptobiphenyl-3-ol

HRID 1987477Notes

Reaction equation

HRID 1987477 reaction equation
COC1C=C(OC)C=C(OC)C=1C[S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C.C(Cl)Cl>O>[SH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 668706052'-(2,4,6-Trimethoxybenzylthio)biphenyl-3-ol

Product 1

HCID 686436712'-Mercaptobiphenyl-3-olYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2′-(2,4,6-trimethoxybenzylthio)biphenyl-3-ol (0.948 g, 2.48 mmol) was treated with TFA:triethylsilane:DCM (8 ml:3 ml:80 ml). The solution was stirred 30 min. before 40 ml water was added and the mixture was extracted with DCM (2×80 ml). The organic was washed with water, brine, dried over magnesium sulfate and concentrated. The residue was purified by silica flash chromatography (hexane:ethyl acetate 80:20) to afford 0.335 g product (1.66 mmol, 67% yield).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with DCM (2×80 ml)
  3. washThe organic was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica flash chromatography (hexane:ethyl acetate 80:20)

Sources & evidence

ORD record
ord-5d66d310ae5a466bac3fa8881e8a5a62
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

Loading…