3,5-Dibromobenzaldehyde → 3,5-Dibromostyrene

HRID 1822315노트

반응식

HRID 1822315 반응식
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([Br:16])[CH:15]=1)[CH:11]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH2:1])[CH:13]=[C:14]([Br:16])[CH:15]=1

참가 물질

5

반응물 2

HCID 6220773,5-DibromobenzaldehydeHCID 23665647Potassium tert-butoxide

생성물 1

HCID 186903433,5-Dibromostyrene수율 46%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of methyltriphenylphosphonium bromide (20.30 g, 56.8 mmol) in dry THF (50 mL) is cooled to 0° C. under N2 and then treated with solid potassium tert-butoxide (6.38 g, 56.8 mmol) in portions. The resultant yellow slurry is warmed to rt and stirred for 30 minutes. The mixture is cooled to −78° C., and a solution of 3,5-dibromobenzaldehyde (10.0 g, 37.9 mmol) in THF (50 mL) is added dropwise. The reaction is warmed to rt and stirred for 1 hour. The mixture is poured into ice water containing 1 N HCl (56 mL) and then extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 10/1 hexanes/ethyl acetate to afford 4.56 g (46%) of the title compound. Rf=0.64 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3).

후처리

  1. temperatureThe mixture is cooled to −78° C.
  2. temperatureThe reaction is warmed to rt
  3. stirringstirred for 1 hour
  4. extractionextracted with Et2O
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. customthe solvent is removed in vacuo
  7. customto afford crude product that
  8. customis absorbed on silica gel
  9. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-67b0a52f5413402b928d475bcc0c1480
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608639B2

반응 노트

불러오는 중…