Water → 6-tert-Butyl-5-methoxy-2-methyl-4-phenylindan-1-one

HRID 716441Notes

Reaction equation

HRID 716441 reaction equation
Br[C:2]1[C:10]([O:11][CH3:12])=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:18])[C:6]2=[O:17].C([O-])([O-])=O.[Na+].[Na+].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[C:13]([C:9]1[CH:8]=[C:7]2[C:3]([CH2:4][CH:5]([CH3:18])[C:6]2=[O:17])=[C:2]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:10]=1[O:11][CH3:12])([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 602106934-Bromo-6-tert-butyl-5-methoxy-2-methyl-1-indanone

Product 1

HCID 712309196-tert-Butyl-5-methoxy-2-methyl-4-phenylindan-1-oneYield 98%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 46.7 g (0.150 mol) of 4-bromo-6-tert-butyl-5-methoxy-2-methylindan-1-one, 44.5 g (0.420 mol) of Na2CO3, 22.0 g (0.180 mol) of PhB(OH)2, 570 ml of DME, and 195 ml of water 0.674 g (3.0 mmol) of Pd(OAc)2 and 1.58 g (6.00 mmol) of PPh3 were added. The resulting mixture was refluxed for 12 h, cooled to room temperature, and then DME was evaporated on Rotavap. To the residue 1 liter of cold water was added, and the crude product was extracted with 3×300 ml of dichloromethane. The combined organic extract was dried over K2CO3 and then evaporated to dryness. The residue after evaporation was extracted with hot hexane (500 ml, then 3×250 ml) and this extracts while hot were passed through a short pad of silicagel, evaporated on Rotavap to yield 45.1 g (98%) of 6-tert-butyl-5-methoxy-2-methyl-4-phenylindan-1-one as a slightly yellowish crystalline solid which was further used without an additional purification.

Workup

  1. additionwere added
  2. temperatureThe resulting mixture was refluxed for 12 h
  3. customDME was evaporated on Rotavap
  4. additionTo the residue 1 liter of cold water was added
  5. extractionthe crude product was extracted with 3×300 ml of dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over K2CO3
  8. customevaporated to dryness
  9. customThe residue after evaporation
  10. extractionwas extracted with hot hexane (500 ml
  11. customevaporated on Rotavap

Sources & evidence

ORD record
ord-e60303ce81dc43329d2cf11be60516c9
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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