Methanol → Tert-butyl 3-bromo-5-(hydroxymethyl)benzoate

HRID 1257524노트

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HRID 1257524 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:15](OC)=[O:16])[CH:5]=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[BH4-].[Na+].CO>O1CCCC1>[Br:1][C:2]1[CH:14]=[C:6]([CH:5]=[C:4]([CH2:15][OH:16])[CH:3]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 66896065Tert-butyl methyl 5-bromoisophthalate

생성물 1

HCID 58096191Tert-butyl 3-bromo-5-(hydroxymethyl)benzoate수율 81.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of tert-butyl methyl 5-bromoisophthalate (3.63 g, 11.5 mmol) in tetrahydrofuran (90 mL) at 0° C. was added portionwise sodium borohydride (1.53 g, 40.3 mmol). The mixture was stirred at 0° C. After 30 min, methanol (4.2 mL, 92.0 mmol) was added and the mixture was heated to 40° C. After 6 h, the mixture was cooled to ambient temperature and the mixture was quenched with methanol and concentrated. Ethyl acetate was added and the mixture was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (2.7 g).

후처리

  1. temperaturethe mixture was heated to 40° C
  2. waitAfter 6 h
  3. temperaturethe mixture was cooled to ambient temperature
  4. customthe mixture was quenched with methanol
  5. concentrationconcentrated
  6. additionEthyl acetate was added
  7. washthe mixture was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-58805491a88f4125a5c9b26f9c6f4aec
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461185B2

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