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

HRID 2367979노트

반응식

HRID 2367979 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 866647343-Ethoxy-6-fluoro-2-hydroxy-benzaldehyde수율 89.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7aefcc4fed0e411585ccf84af0939f53
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703742B2

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