Hydrochloric Acid → (3-Bromo-5-iodophenyl)methanol

HRID 378169

반응식

HRID 378169 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([I:11])[CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>C(Cl)Cl>[Br:10][C:8]1[CH:7]=[C:6]([I:11])[CH:5]=[C:4]([CH:9]=1)[CH2:3][OH:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 21942573Methyl 3-bromo-5-iodobenzoate

생성물 1

HCID 15467379(3-Bromo-5-iodophenyl)methanol수율 96.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To methyl 5-bromo-3-iodobenzoate (Step A above) (5.01 g, 0.015 mole) in anhydrous methylene chloride (100 mL) at -78° C., was added dropwise minutes, diisobutylaluminum hydride (5.50 mL, 0.03 mole). The mixture was stirred for 1 hour then allowed to warm to 0° C. The reaction solution was poured into 600 mL, chilled 3N HCl and extracted 3× with methylene chloride (150 mL). The organic layers were combined, dried over MgSO4 and concentrated under vacuum to yield 5-bromo-3-iodobenzyl alcohol (4.54 g) as a white solid. MP=110-112° C. MS and NMR were consistent with the desired structure.

후처리

  1. additionThe reaction solution was poured into 600 mL
  2. extractionextracted 3× with methylene chloride (150 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-7a3136ee0bb84c16864a250cede4929f
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06028223

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