Sodium Carbonate → 6-tert-Butyl-4-(4-tert-butylphenyl)-5-methoxy-2-methylindan-1-one

HRID 716464Notes

Reaction equation

HRID 716464 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:19]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O.COCCOC.CC([O-])=O.CC([O-])=O.[Pd+2]>[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:26]2[CH:27]=[CH:28][C:23]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:24][CH:25]=2)[C:10]=1[O:11][CH3:12])([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343204-tert-Butylphenylboronic acidHCID 602106934-Bromo-6-tert-butyl-5-methoxy-2-methyl-1-indanone

Product 1

HCID 712308126-tert-Butyl-4-(4-tert-butylphenyl)-5-methoxy-2-methylindan-1-oneYield 81%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 31.1 g (100 mmol) of 4-bromo-6-tertbutyl-5-methoxy-2-methylindanone, 25.0 g (140 mmol) of 4-tert-butylphenylboronic acid, 29.4 g (280 mmol) of Na2CO3, 1.35 g (6.00 mmol, 6 mol. %) of Pd(OAc)2, and 3.15 g (12.0 mmol, 12 mol. %) of PPh3 in 130 ml of water and 380 ml of DME was refluxed for 6 h in argon atmosphere. The formed mixture was evaporated to dryness. To the residue 500 ml of dichloromethane and 500 ml of water were added. The organic layer was separated, the aqueous layer was additionally extracted with 100 ml of dichloromethane. The combined organic extract was dried over Na2SO4, evaporated to dryness, and the crude product was isolated using flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-dichloromethane=2:1, vol.). This crude product was recrystallized from n-hexane to give 29.1 g (81%) of a white solid.

Workup

  1. temperaturewas refluxed for 6 h in argon atmosphere
  2. customThe formed mixture was evaporated to dryness
  3. additionTo the residue 500 ml of dichloromethane and 500 ml of water were added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was additionally extracted with 100 ml of dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over Na2SO4
  8. customevaporated to dryness
  9. customthe crude product was isolated
  10. customThis crude product was recrystallized from n-hexane

Sources & evidence

ORD record
ord-b984815d1d4c43bd9784b722aa5f9829
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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