Dibromomethane → HCID 86657577, compound

HRID 1471873Notes

Reaction equation

HRID 1471873 reaction equation
[C:1]1([C:7](=[O:15])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])(C)C.[K+].[C:22](=[S:24])=[S:23].Br[CH2:26]Br>C1COCC1>[S:23]1[CH2:26][S:24][C:22]1=[C:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:15]

Participants

6

Reactant 4

HCID 3024DibromomethaneHCID 6348Carbon DisulfideHCID 99482-PhenylacetophenoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 86657577HCID 86657577, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2-diphenylethanone (10.0 g, 51.0 mmol) in anhydrous THF (100 mL) was added KOtBu (1M in THF, 51.0 mL, 51.0 mmol). The mixture was stirred for 30 min at room temperature, and carbon disulfide (7.76 g, 102 mmol) was added. After 10 min, dibromomethane (17.72 g, 102 mmol) was added and the reaction was stirred for 4 h at room temperature. The reaction was quenched with water (10 mL) and diluted with EtOAc. The organic layer was separated, dried over MgSO4, and concentrated to give the title compound as a yellow solid (13.0 g). LCMS m/z=285.0 [M+H]+.

Workup

  1. waitAfter 10 min
  2. stirringthe reaction was stirred for 4 h at room temperature
  3. customThe reaction was quenched with water (10 mL)
  4. additiondiluted with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3695c2aaa0fc427ebd9b674927be5154
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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