Hydrochloric Acid → 4-bromo-2-(hydroxymethyl)-6-methoxyphenol

HRID 655650

반응식

HRID 655650 반응식
[BH4-].[Na+].C1COCC1.[Br:8][C:9]1[CH:10]=[C:11]([O:18][CH3:19])[C:12]([OH:17])=[C:13]([CH:16]=1)[CH:14]=[O:15].Cl>C(O)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([O:18][CH3:19])[C:12]([OH:17])=[C:13]([CH2:14][OH:15])[CH:16]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehydeHCID 4311764Sodium borohydride

생성물 1

HCID 8940924-bromo-2-(hydroxymethyl)-6-methoxyphenol수율 100.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
0 °C

실험 절차

Sodium borohydride (0.28 g, 6.9 mmol) was added to a THF solution (30 ml) of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (3.2 g 13.8 mmol) under ice cooling and the mixture was stirred at 0° C. for 2 hours. Acetic acid was added to the reaction solution to set pH at 3. 10% hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The extracted material was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→1:1) and concentrated to dryness under reduced pressure to obtain 4-bromo-2-hydroxymethyl-6-methoxyphenol (3.23 g) as light yellow oil.

후처리

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe extracted material was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→1:1)
  5. concentrationconcentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-ccc54352225947aa9aa1a81d6c3026d5
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071600B2

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