Sodium Carbonate → HCID 90422969, compound

HRID 2272452Notes

Reaction equation

HRID 2272452 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([O:14][C:15]1[CH:24]=[C:23]([CH:25]2[CH2:28][CH2:27][CH2:26]2)[CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:29]Br.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:7]([O:14][C:15]1[CH:24]=[C:23]([CH:25]2[CH2:28][CH2:27][CH2:26]2)[C:22]([Br:29])=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 516892Sodium BicarbonateHCID 90423580HCID 90423580, compound

Product 1

HCID 90422969HCID 90422969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium carbonate (7.51 g) was added to a dichloromethane (150 mL) solution of methyl 2-(benzyloxy)-4-cyclobutylbenzoate (14 g), then a dichloromethane (25 mL) solution of bromine (3.17 mL) was slowly added thereto at 10 C, and the mixture was stirred at the same temperature as above for 1 hour. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture, followed by extraction with ethyl acetate twice. The obtained organic layer was washed with a saturated aqueous solution of sodium bisulfite and saturated saline in this order and dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (12.2 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washThe obtained organic layer was washed with a saturated aqueous solution of sodium bisulfite and saturated saline in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-87470b8bdd9f4f57a41606d53b662087
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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