Ethanol → Diethyl 5-bromo-1H-indene-2,2(3H)-dicarboxylate

HRID 1057151Notes

Reaction equation

HRID 1057151 reaction equation
[H-].[Na+].CCO.[C:6]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[C:20]([CH2:26]Br)[CH:19]=1>CCOCC>[Br:17][C:18]1[CH:19]=[C:20]2[C:21](=[CH:22][CH:23]=1)[CH2:24][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])([C:6]([O:14][CH2:15][CH3:16])=[O:13])[CH2:26]2

Participants

6

Reactant 4

HCID 702EthanolHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 124964654-Bromo-1,2-bis(bromomethyl)benzene

Product 1

HCID 66802690Diethyl 5-bromo-1H-indene-2,2(3H)-dicarboxylateYield 72.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium hydride (60% in mineral oil, 123 mg, 3.1 mmol) was added in small portions to EtOH (2 mL) in Et2O (6 mL) at room temperature under N2. After the addition was complete, the nearly clear and colorless solution was stirred for 5 min. To this solution, diethyl malonate (234 mg, 1.46 mmol) was added followed by the addition of 4-bromo-1,2-bis(bromomethyl)benzene (500 mg, 1.46 mmol). Immediately, a precipitate was formed, and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified on silica gel column using 0-10% EtOAc in petroleum ether to afford the title compound (360 mg, 72%). 1HNMR (400 MHz, DMSO-d6): δ 7.44 (d, 1H), 7.35 (d, 1H), 7.20-7.18 (m, 1H), 4.15 (q, 4H), 3.48 (s, 2H), 3.43 (s, 2H), 1.16 (t, 6H).

Workup

  1. additionAfter the addition
  2. customImmediately, a precipitate was formed
  3. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-a0623701f55045e980148dc607ce98c9
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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