Sodium borohydride → 1-Bromo-3-fluorobenzyl alcohol

HRID 1670596노트

반응식

HRID 1670596 반응식
[Br:1][C:2]1([CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH2:5]1)[CH:3]=[O:4].[BH4-].[Na+]>CO.C(OCC)(=O)C>[Br:1][C:2]1([CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH2:5]1)[CH2:3][OH:4]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 866319341-Bromo-3-fluorobenzaldehyde

생성물 1

HCID 673357701-Bromo-3-fluorobenzyl alcohol수율 100%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To 1-bromo-3-fluorobenzaldehyde (1.60 kg, 7.91 mol) in methanol (14 L) at 0° C. add sodium borohydride (284 g, 7.93 mol) in portions over 30 min to control the exotherm and gas evolution. After 15 min, quench with water (500 mL) and concentrate to obtain a yellow oil. Dissolve the oil in ethyl acetate (6 L) and wash with water (3 L). Extract the aqueous layer with ethyl acetate (1 L). Wash the combined organic phases with brine (2 L), dry over sodium sulfate, filter, and concentrate to obtain the title compound as an orange oil (1614 g, 100%). 1H NMR (CDCl3) δ 7.40 (d, 1H), 7.18 (m, 1H), 7.07 (t, 1H), 4.86 (s, 2H).

후처리

  1. customquench with water (500 mL)
  2. concentrationconcentrate
  3. customto obtain a yellow oil
  4. washwash with water (3 L)
  5. extractionExtract the aqueous layer with ethyl acetate (1 L)
  6. washWash the combined organic phases with brine (2 L)
  7. dry with materialdry over sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate

출처 및 근거

ORD 기록
ord-5d0c13cdd0a249bb8b46752edce60c5b
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994164B2

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