Methyl 2-bromo-4-methylbenzoate → Methyl 2-isopropyl-4-methylbenzoate

HRID 541312

반응식

HRID 541312 반응식
[CH:1]([Mg]Br)([CH3:3])[CH3:2].Br[C:7]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]>C1COCC1.Br[Zn]Br.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:1]([C:7]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])([CH3:3])[CH3:2]

참가 물질

6

반응물 2

HCID 21779704Methyl 2-bromo-4-methylbenzoateHCID 178418365HCID 178418365, 화합물

생성물 1

HCID 68288614Methyl 2-isopropyl-4-methylbenzoate

시약·촉매·용매 3

HCID 24375Zinc bromide (ZnBr2); Zinc Dibromide촉매HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-48 °C

실험 절차

To a stiffed mixture of dibromozinc (39.0 g, 173 mmol, 4.00 equiv) in THF (500 mL) under nitrogen at −48° C. was added dropwise isopropylmagnesium bromide (3 M in THF, 170 mmol) over a period of 30 min Pd(dppf)Cl2 (0.5 g, 0.05 equiv) and methyl 2-bromo-4-methylbenzoate (10.0 g, 43.7 mmol, 1.00 equiv) were added to the above reaction mixture. After stirring for 1 h at −48° C., the reaction mixture was quenched by the careful addition of 500 mL of NH4Cl (aq.). The resulting mixture was extracted with 3×500 mL of ethyl acetate. The combined organic layers were washed with 3×500 mL of brine and concentrated in vacuo. The residue was purified using silica gel column chromatography with petroleum ether (1:1) as eluent. This resulted in 6.50 g (77%) of methyl 2-isopropyl-4-methylbenzoate as a yellow oil.

후처리

  1. additionwere added to the above reaction mixture
  2. customthe reaction mixture was quenched by the careful addition of 500 mL of NH4Cl (aq.)
  3. extractionThe resulting mixture was extracted with 3×500 mL of ethyl acetate
  4. washThe combined organic layers were washed with 3×500 mL of brine
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. customThis resulted in 6.50 g (77%) of methyl 2-isopropyl-4-methylbenzoate as a yellow oil

출처 및 근거

ORD 기록
ord-20212813c911466ab351572052110faf
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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