Sodium Carbonate → Benzyl 2-benzyloxy-5-cyanobenzoate

HRID 1639535Notes

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

Participants

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

extractionextracted several times with ethyl acetate
washCombined extracts are washed with brine
dry with materialdried over Na2SO4
customAfter solvent removal by rotoevaporation
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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