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

HRID 1257524ノート

反応式

HRID 1257524 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-58805491a88f4125a5c9b26f9c6f4aec
出典データセット
uspto-grants-2013_06
特許番号
US08461185B2

反応ノート

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