4-Bromo-2-chlorobenzoic acid → (4-Bromo-2-chlorophenyl)methanol

HRID 40274

반응식

HRID 40274 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([Cl:11])[CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([Cl:11])[CH:3]=1

참가 물질

3

반응물 1

HCID 1088294-Bromo-2-chlorobenzoic acid

생성물 1

HCID 43805739(4-Bromo-2-chlorophenyl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirring solution of 4-bromo-2-chlorobenzoic acid (11.1 g, 47 mmol) in THF (100 mL) at 0° C. under nitrogen was added borane-methyl sulfide complex (9.4 ml, 94 mmol) via syringe over 10 min. Gas evolution quite evident. Ice bath removed, and once gas evolution subsided reaction gently heated to reflux for 1 h. Reaction slowly quenched with MeOH (50 mL) and 2M HCl (20 mL). Aqueous extracted with 9:1 CHCl3/IPA (150 mL). Organic dried with sat NH4Cl, MgSO4, then concentrated to a colorless oil under reduced pressure. Product crystallized after 1 week sitting neat.

후처리

  1. customIce bath removed
  2. customreaction
  3. temperaturegently heated
  4. temperatureto reflux for 1 h
  5. customReaction
  6. customslowly quenched with MeOH (50 mL) and 2M HCl (20 mL)
  7. extractionAqueous extracted with 9:1 CHCl3/IPA (150 mL)
  8. dry with materialOrganic dried with sat NH4Cl, MgSO4
  9. concentrationconcentrated to a colorless oil under reduced pressure
  10. customProduct crystallized after 1 week

출처 및 근거

ORD 기록
ord-a5ee826e352540d6b4248f3334706d32
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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