Hydrochloric Acid → HCID 67957245, compound

HRID 571558Notes

Reaction equation

HRID 571558 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:7]4[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:8]=4[C:9]([OH:17])=[CH:10][C:11]=3[C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].Cl>O.C(COC)OC>[CH3:23][O:22][C:20]1[CH:19]=[CH:18][C:8]2[C:9]([OH:17])=[CH:10][C:11]3[C:12]([CH3:15])([CH3:16])[C:13]4[CH:14]=[C:2]([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=5[O:25][CH3:24])[CH:3]=[CH:4][C:5]=4[C:6]=3[C:7]=2[CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 67957464HCID 67957464, compound

Product 1

HCID 67957245HCID 67957245, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

The product of Step 3 of Example 5, (9-bromo-2-methoxy-7,7-dimethyl-7H-benzo[c]fluoren-5-ol (6 g)) and 2-methoxyphenyl boronic acid (2.8 g) were added to a solution of dimethoxyethane (40 mL) and water (20 mL) in a 250 mL round bottom 3-necked flask, followed by addition of Na2CO3 (3.5 g). The resulting solution was bubbled with nitrogen for 10 minutes and then the Palladium catalyst, Pd[PPh3]4, 0.5 g, was added to the reaction mixture. Then the reaction mixture heat to reflux temperatures under a nitrogen atmosphere. The reaction was monitored by TLC analysis. By the end of reaction, the reaction was cooled to room temperature and quenched by adding water (30 mL). The pH of reaction mixture was adjusted to 5-6 by adding hydrochloric acid (37%, 7.5 g) slowly. The product was extracted with ethyl acetate (2×50 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated by rotary evaporation to yield the product, 2-methoxy-9-(2-methoxyphenyl)-7,7-dimethyl-7H-benzo[c]fluoren-5-ol (5.7 g) which was used for next reaction as is.

Workup

  1. customThe resulting solution was bubbled with nitrogen for 10 minutes
  2. additionthe Palladium catalyst, Pd[PPh3]4, 0.5 g, was added to the reaction mixture
  3. temperatureThen the reaction mixture heat
  4. temperatureto reflux temperatures under a nitrogen atmosphere
  5. customBy the end of reaction
  6. customquenched
  7. additionby adding water (30 mL)
  8. customThe pH of reaction mixture
  9. extractionThe product was extracted with ethyl acetate (2×50 mL)
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-ae5c3efde0c543f5847802350c17695d
Source dataset
uspto-grants-2015_05
Patent number
US09028728B2

Reaction notes

Loading…