Bromine → 4-Bromo-6-tert-butyl-5-methoxy-2-methyl-1-indanone

HRID 1174080Notes

Reaction equation

HRID 1174080 reaction equation
[Br:1]Br.[C:3]([C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH:12]([CH3:17])[C:13]2=[O:16])=[CH:9][C:8]=1[O:18][CH3:19])([CH3:6])([CH3:5])[CH3:4].CC([O-])=O.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:1][C:9]1[C:8]([O:18][CH3:19])=[C:7]([C:3]([CH3:4])([CH3:6])[CH3:5])[CH:15]=[C:14]2[C:10]=1[CH2:11][CH:12]([CH3:17])[C:13]2=[O:16]

Participants

7

Reactant 3

HCID 24408Bromine2×HCID 517045Sodium Acetate2×HCID 601502696-(tert-Butyl)-5-methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 602106934-Bromo-6-tert-butyl-5-methoxy-2-methyl-1-indanone

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Bromine (4.4 ml, 86 mmol) was added at 0° C. to a mixture of 6-tert-butyl-5-methoxy-2-methyl-1-indanone (20 g, 86 mmol), NaOAc (20.4 g) and tetrabutylammonium bromide (0.5 g) in CH2Cl2 (50 ml) and H2O (150 ml). After 16 h, 2.5 ml of Br2 and 12 g of NaOAc were added. After 24 h of stirring, the organic phase was separated, washed with water, 10% aq. Na2SO3, aq. NaHCO3, dried over MgSO4 and evaporated. The residue was used without purification.

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 used without purification

Sources & evidence

ORD record
ord-86e75f4673cc4d1f9b0ce4b5fea57200
Source dataset
uspto-grants-2010_11
Patent number
US07834205B2

Reaction notes

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