Cesium carbonate → 3-(Phenylmethoxy)-4-[(4-trifluoromethylphenyl)methoxy]benzaldehyde

HRID 2213567Notes

Reaction equation

HRID 2213567 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[CH2:13]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[OH:29])[CH:24]=[O:25])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[C:14]1([CH2:13][O:20][C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=2[O:29][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=2)[CH:24]=[O:25])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 110206353-Benzyloxy-4-hydroxybenzaldehyde

Product 1

HCID 219574953-(Phenylmethoxy)-4-[(4-trifluoromethylphenyl)methoxy]benzaldehydeYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Trifluoromethylbenzyl bromide (0.17 mL, 1.09 mmol, 1 eq) was added dropwise to a stirred solution of 3-benzyloxy-4-hydroxybenzaldehyde (250 mg, 1.09 mmol, 1 eq) and cesium carbonate (357 mg, 1.09 mmol, 1 eq) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred overnight, then diluted with ethyl acetate (30 mL) and washed sequentially with water (4×30 mL), 0.5M aqueous sodium hydroxide (30 mL), 10% HCl and brine. The organic solution was dried over sodium sulfate and evaporated in vacuo to give the product as a white powder (422 mg, 99%). 1H NMR (CDCl3) δ 9.82 (s, 1H, O═C—H), 5.28 (2H, s, CH2Ar), 5.21 (s, 2H, CH2Ph).

Workup

  1. washwashed sequentially with water (4×30 mL), 0.5M aqueous sodium hydroxide (30 mL), 10% HCl and brine
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-98c037bea44a46479f90b1ca54aea9f3
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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