Dimethyl Ether → HCID 67608446, compound

HRID 2280842Notes

Reaction equation

HRID 2280842 reaction equation
[CH3:1][O:2][C:3]1[C:23]([O:24][CH3:25])=[CH:22][C:6]2[C:7]([OH:21])=[CH:8][C:9]3[C:10]([CH3:20])([CH3:19])[C:11]4[CH:12]=[C:13](Br)[CH:14]=[CH:15][C:16]=4[C:17]=3[C:5]=2[CH:4]=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].COC>O>[CH3:1][O:2][C:3]1[C:23]([O:24][CH3:25])=[CH:22][C:6]2[C:7]([OH:21])=[CH:8][C:9]3[C:10]([CH3:20])([CH3:19])[C:11]4[CH:12]=[C:13]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=5[O:27][CH3:26])[CH:14]=[CH:15][C:16]=4[C:17]=3[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 8254Dimethyl EtherHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 66610516HCID 66610516, compound

Product 1

HCID 67608446HCID 67608446, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL single-neck flask was added 2,3-dimethoxy-7,7-dimethyl-9-bromo-7H-benzo[C]fluoren-5-ol (10 g) prepared according to the first five steps of example 1 in US 2006/0226402 which is included herein as reference, 2-methoxyphenylboronic acid (4.3 g), sodium carbonate (5.9 g), dimethyl ether (120 mL) and water (24 mL). The mixture was purged with N2 for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.6 g) was added to the mixture. The reaction mixture was heated to reflux for 18 hours. The mixture was cooled to room temperature and poured into water (180 mL). The resulting mixture was extracted with ethyl acetate (100 mL). The top layer was dried over sodium sulfate and then condensed to lesser volume. Solid 2,3-dimethoxy-7,7-dimethyl-9-(2-methoxyphenyl)-7H-benzo[C]fluoren-5-ol (10 g) was obtained by recrystallization from solution in t-butyl methyl ether/hexanes.

Workup

  1. customprepared
  2. customThe mixture was purged with N2 for 15 minutes
  3. additionTetrakis(triphenylphosphine)palladium(0) (0.6 g) was added to the mixture
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux for 18 hours
  6. additionpoured into water (180 mL)
  7. extractionThe resulting mixture was extracted with ethyl acetate (100 mL)
  8. dry with materialThe top layer was dried over sodium sulfate
  9. customcondensed to lesser volume

Sources & evidence

ORD record
ord-70791915ab06496b895e2f9c90738d0e
Source dataset
uspto-grants-2015_09
Patent number
US09139552B2

Reaction notes

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