Bromine → HCID 60210697, compound

HRID 1174082Notes

Reaction equation

HRID 1174082 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[CH3:14])[C:10](=[O:15])[CH:9]([CH3:16])[CH2:8]2.CC([O-])=O.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:1][C:6]1[C:5]([O:4][CH3:3])=[C:13]([CH3:14])[CH:12]=[C:11]2[C:7]=1[CH2:8][CH:9]([CH3:16])[C:10]2=[O:15]

Participants

7

Reactant 3

HCID 24408Bromine2×HCID 517045Sodium Acetate2×HCID 60210696HCID 60210696, compound

Product 1

HCID 60210697HCID 60210697, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Bromine (6 mL, 11.7 mmol) was added at 0° C. to a mixture of 5-methoxy-2,6-dimethyl-1-indanone (22 g, 11.7 mmol), NaOAc (27 g) and tetrabutylammonium bromide (0.5 g) in CH2Cl2 (100 mL) and H2O (200 mL). After 16 h, 1 mL of Br2 and 6 g of NaOAc were added. After 24 h stirring, the organic phase was separated, washed with water, 10% aq. Na2SO3, aq. NaHCO3, dried over MgSO4 and evaporated. The residue was recrystallized from hexane. Yield=24.7 g (78.4%).

Workup

  1. customthe organic phase was separated
  2. washwashed with water, 10% aq. Na2SO3, aq. NaHCO3
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-1523130996b6482382f5c9eed72e580a
Source dataset
uspto-grants-2010_11
Patent number
US07834205B2

Reaction notes

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