Ethyl Bromide → 3-Ethoxy-6-fluoro-2-hydroxy-benzaldehyde

HRID 2367979ノート

反応式

HRID 2367979 の反応式
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH2:12](Br)[CH3:13]>CS(C)=O.O>[CH2:12]([O:11][C:5]1[C:6]([OH:10])=[C:7]([C:2]([F:1])=[CH:3][CH:4]=1)[CH:8]=[O:9])[CH3:13]

参加物

5

反応物 2

HCID 6332Ethyl BromideHCID 866647326-Fluoro-2,3-dihydroxybenzaldehyde

生成物 1

HCID 866647343-Ethoxy-6-fluoro-2-hydroxy-benzaldehyde収率 89.1%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

To a solution of 6-fluoro-2,3-dihydroxy-benzaldehyde (1.00 g, 6.40 mmol) in dry DMSO (10 mL) was added NaOBut (1.23 g, 12.81 mmol) and ethyl bromide (0.77 g, 7.04 mmol) under N2 and stirred at RT for 18 h. The resultant mixture was diluted with water, acidified to pH ˜6 with 2N.HCl and extracted with EtOAc (4×25 mL). Combined organic layers were washed with water and brine and dried over MgSO4. Filtration and removal of the solvent under reduced pressure provided 1.05 g (5.70 mmol, 89%) of the title compound as yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.24 (s, 1H), 7.04 (dd, J=8.8, 5.3 Hz, 1H), 6.61-6.50 (m, 1H), 4.09 (q, J=7.0 Hz, 3H), 1.46 (t, J=7.0 Hz, 3H); 19F NMR (376 MHz, CHLOROFORM-d) δ ppm −132.19-−132.15 (m, 1F).

後処理

  1. extractionHCl and extracted with EtOAc (4×25 mL)
  2. washCombined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and removal of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-7aefcc4fed0e411585ccf84af0939f53
出典データセット
uspto-grants-2014_04
特許番号
US08703742B2

反応ノート

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