Cesium carbonate → 2,4-Difluorobenzyl 2-(2,4-difluorobenzyloxy)-5-formylbenzoate

HRID 1583033Notes

Reaction equation

HRID 1583033 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Br.[CH:11]([C:13]1[CH:21]=[C:17]([C:18]([OH:20])=[O:19])[C:16]([OH:22])=[CH:15][CH:14]=1)=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][O:22][C:16]1[CH:15]=[CH:14][C:13]([CH:11]=[O:12])=[CH:21][C:17]=1[C:18]([O:20][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=1[F:1])=[O:19]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 692265-Formylsalicylic acidHCID 902971-(Bromomethyl)-2,4-difluorobenzene

Product 1

HCID 227168172,4-Difluorobenzyl 2-(2,4-difluorobenzyloxy)-5-formylbenzoateYield 95.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4-Difluorobenzyl bromide (0.77 mL, 6 mmol, 1 eq) was added dropwise to a stirred solution of 5-formylsalicylic acid (1 g, 6 mmol, 1 eq) and cesium carbonate (5.87 g, 18 mmol, 3 eq) in N,N-dimethylformamide (30 mL). The reaction mixture was diluted with ethyl acetate (50 mL) and the organic solution washed with water (50 mL), saturated aqueous sodium bicarbonate (2×50 mL) and brine (50 mL), then dried over sodium sulfate and evaporated in vacuo to give the product as a white powder (1.2 g, 50%). 1H NMR (CDCl3) δ9.91 (s, 1H, O═C—H), 5.37 (s, 2H, CH2Ar), 5.25 (s, 2H, CH2Ar).

Workup

  1. washthe organic solution washed with water (50 mL), saturated aqueous sodium bicarbonate (2×50 mL) and brine (50 mL)
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-5a39090d72e74ba4ae6fc6d10532acc2
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

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