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Sodium Carbonate → Benzyl 2-benzyloxy-5-cyanobenzoate

HRID 1639535
Notes
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Reaction equation

HRID 1639535 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:22](Br)=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].C[C:33]([N:35](C)C)=O>O.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.O.O.O.[K+].[K+].[K+].[K+].[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:22]([C:33]#[N:35])=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

Product 1

HCID 18974028Benzyl 2-benzyloxy-5-cyanobenzoateYield 72%

Reagents, catalysts & solvents 3

HCID 161067Potassium ferrocyanide trihydrateCatalyst
HCID 167845
palladium(II) acetate
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 695 mg (1.76 mmol) of benzyl 2-benzyloxy-5-bromobenzoate, 175 mg (0.41 mmol) of potassium hexacyanoferrate(II) trihydrate, 41 mg (0.8 mmol) of palladium(II) acetate, and 189 mg (1.75 mmol) of sodium carbonate in 3 mL of dimethylacetamide is heated at 120° C. for 24 hrs. The reaction mixture is diluted with water and extracted several times with ethyl acetate. Combined extracts are washed with brine and dried over Na2SO4. After solvent removal by rotoevaporation, the crude product is purified by preparative TLC to give 436 mg (1.27 mmol, 72% yield) of benzyl 2-benzyloxy-5-cyanobenzoate.

Workup

  1. extractionextracted several times with ethyl acetate
  2. washCombined extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter solvent removal by rotoevaporation
  5. customthe crude product is purified by preparative TLC

Sources & evidence

ORD record
ord-05281bd2597847fd9a7a65b38c57c19f
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08110570B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes