Carbon tetrabromide → 3-[2-Bromomethyl-4-(tert-butyldiphenylsilanyloxy)phenyl]propionic acid tert-butyl ester

HRID 1181124노트

반응식

HRID 1181124 반응식
[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:33]O)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:56]>C1COCC1>[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:33][Br:56])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 589792063-[4-(tert-Butyldiphenylsilanyloxy)-2-hydroxymethylphenyl]propionic acid tert-butyl ester

생성물 1

HCID 589793453-[2-Bromomethyl-4-(tert-butyldiphenylsilanyloxy)phenyl]propionic acid tert-butyl ester수율 86.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A 200 mL round bottomed flask was charged with 3-[4-(tert-butyldiphenylsilanyloxy)-2-hydroxymethylphenyl]propionic acid tert-butyl ester (3.03 g, 6.18 mmol), anhydrous THF (75 mL), and then triphenylphosphine (3.24 g, 12.4 mmol) and CBr4 (4.10 g, 12.4 mmol). The yellow mixture was stirred at ambient temperature under a nitrogen atmosphere for 1 h and was concentrated. The residue was diluted with EtOAc (500 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated to a solid. The crude product was purified using a Biotage medium pressure chromatography system (EtOAc:hexanes 10:90) to give a yellow oil (2.95 g, 86%), MS (ES) m/e 572 (M+NH4).

후처리

  1. concentrationwas concentrated
  2. additionThe residue was diluted with EtOAc (500 mL)
  3. washThe organic layer was washed with brine (2×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a solid
  6. customThe crude product was purified

출처 및 근거

ORD 기록
ord-30d82aef0da1469092a2e1dfed64bf8c
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282501B2

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