3,4-Dihydroxybenzaldehyde → 4-(Difluoromethoxy)-3-hydroxybenzaldehyde

HRID 3021

反応式

HRID 3021 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].Cl[C:12]([F:18])([F:17])C(OC)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:17][CH:12]([F:18])[O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[OH:1]

参加物

5

反応物 3

HCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 73935Methyl chlorodifluoroacetate

生成物 1

HCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehyde収率 38%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3,4-Dihydroxybenzaldehyde (0.50 g, 3.62 mmol, Aldrich), methyl chlorodifluoroacetate (0.52 g, 3.62 mmol, Aldrich) and potassium carbonate (0.50 g, 3.62 mmol) were combined in DMF (5.0 mL) under an argon atmosphere. After stirring at 60°-65° C. for 3 h, DMF was removed in vacuo and the residue was partioned between aqueous 3N HCl and ether. The aqueous layer was extracted three times with ether. The combined organic extracts were washed with water, with brine, were dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes) to provide the title compound as a white solid (0.20 g, 38%). mp 83°-85° C.

後処理

  1. customDMF was removed in vacuo
  2. extractionThe aqueous layer was extracted three times with ether
  3. washThe combined organic extracts were washed with water, with brine
  4. dry with materialwere dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-e57e5ba30ba5446d9ef33fda5e7bc0ab
出典データセット
uspto-grants-1998_03
特許番号
US05731477

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