Methanol → HCID 58473636, compound

HRID 2282349Notes

Reaction equation

HRID 2282349 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:22][CH2:23][C:24]([O:26]C)=[O:25])([CH2:16][CH2:17][C:18]([O:20]C)=[O:19])[C:4]=2[CH:3]=1.C1COCC1.CO.[OH-].[Na+]>O>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22475898HCID 22475898, compound

Product 1

HCID 58473636HCID 58473636, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Dimethyl 3,3′-(2,7-dibromo-9H-fluorene-9,9-diyl)dipropanoate (1.23 g, 2.5 mmol) is transferred to a small round bottom flask equipped with a Teflon-coated stirbar. A mixture of THF:MeOH:H2O, 3:2:1, (10 mL) is added and the mixture is stirred for 1 hr. Then a 1 mL portion of 1M NaOH (aq) is added and the mixture is stirred overnight. The next day the water layer is isolated and extracted with 20 mL portions diethyl ether three times. Next the water layer is acidified to ˜pH 2. The water layer is extracted three times with 20 mL portions of dichloromethane. The organic layers are combined and dried with Mg2SO4. The organic solution is filtered and the solvent evaporated to obtain the product as an off-white solid (948 mg, 90% yield).

Workup

  1. stirringthe mixture is stirred overnight
  2. extractionextracted with 20 mL portions diethyl ether three times
  3. extractionThe water layer is extracted three times with 20 mL portions of dichloromethane
  4. dry with materialdried with Mg2SO4
  5. filtrationThe organic solution is filtered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-b38816340bb54b69b666f52a9e41981d
Source dataset
uspto-grants-2015_09
Patent number
US09139869B2

Reaction notes

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