Sodium Carbonate → HCID 71230807, compound

HRID 716475Notes

Reaction equation

HRID 716475 reaction equation
Br[C:2]1[C:10]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[C:9]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:21])[C:6]2=[O:20].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC.O>[C:16]([C:9]1[CH:8]=[C:7]2[C:3]([CH2:4][CH:5]([CH3:21])[C:6]2=[O:20])=[C:2]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]=1[O:11][CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:19])([CH3:18])[CH3:17]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 71230813HCID 71230813, compound

Product 1

HCID 71230807HCID 71230807, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 48.4 g (137 mmol) of 4-bromo-5-isobutoxy-6-tertbutyl-2-methylindanone, 25.0 g (205 mmol) of phenylboronic acid, 40.5 g (382 mmol) of Na2CO3, 1.90 g (8.22 mmol, 6 mol %) of Pd(OAc)2, 4.30 g (16.4 mmol, 12 mol %) of PPh3, 180 ml of water, and 520 ml of DME was refluxed for 6 h. Then, this reaction mixture was quenched with water, solvents were evaporated. The residue was dissolved in 500 ml of dichloromethane, this solution was washed with 500 ml of water. The organic layer was separated, the aqueous layer was additionally extracted with 100 ml of dichloromethane. The combined organic extract was evaporated to dryness, the crude product was obtained from the residue by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-dichloromethane=2:1, vol.). This crude product was re-crystallized from n-hexane to give 40.3 g (84%) as a white solid.

Workup

  1. temperaturewas refluxed for 6 h
  2. customThen, this reaction mixture was quenched with water, solvents
  3. customwere evaporated
  4. dissolutionThe residue was dissolved in 500 ml of dichloromethane
  5. washthis solution was washed with 500 ml of water
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was additionally extracted with 100 ml of dichloromethane
  8. extractionThe combined organic extract
  9. customwas evaporated to dryness

Sources & evidence

ORD record
ord-80b7ebbf988b45a8b035b3b8f55f33da
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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