Dichloromethane → HCID 11984183, compound

HRID 1814163Notes

Reaction equation

HRID 1814163 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([S:14](Cl)(=O)=O)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[Sn].C(Cl)Cl>CO.Cl.O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:9]=[CH:10][C:11]([SH:14])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1)=[O:4]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 5352426Tin atomHCID 23112079HCID 23112079, compound

Product 1

HCID 11984183HCID 11984183, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

The above product 36B (1.0 g, 3.64 mmol) was refluxed with tin powder (2.2 g, 18.8 mmol) in MeOH (10 mL) and 4M HCl/dioxane (10 mL). After 3 h, the reaction mixture was poured into ice with CH2Cl2 (100 mL). The phases were separated and the aqueous layer was extracted with CH2Cl2 (2×50 mL). The combined organic layers were dried with magnesium sulfate, filtered and evaporated to give the thiol compound 36C as a yellow oil (650 mg, 86%). MS: 207 (M−1)+. Step 4. Preparation of (4′-Trifluoromethyl-biphenyl-4-yl)-methanol (Compound 36D)

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (2×50 mL)
  3. dry with materialThe combined organic layers were dried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-74b5c1f4e3434ba2a6eb704f6565de3d
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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