Thionyl Chloride → tert-Butyl [4-(chloromethyl)phenyl]carbamate

HRID 2067334노트

반응식

HRID 2067334 반응식
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1.S(Cl)([Cl:19])=O>ClCCl.N1C=CC=CC=1>[Cl:19][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 10242688Boc-4-aminobenzylalcohol

생성물 1

HCID 46835249tert-Butyl [4-(chloromethyl)phenyl]carbamate수율 50%

시약·촉매·용매 2

HCID 1049Pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)-phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H).

후처리

  1. customThe resulting reaction mixture
  2. customquenched with water (25 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (50 mL)
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3e98fc89cd874f068a4dfc2132c2176b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293768B2

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