Boron Trichloride → Methyl 4-(3,5-dichloro-4-hydroxybenzamido)benzoate

HRID 62716노트

반응식

HRID 62716 반응식
C([O:8][C:9]1[C:27]([Cl:28])=[CH:26][C:12]([C:13]([NH:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=[O:14])=[CH:11][C:10]=1[Cl:29])C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[Cl:28][C:27]1[CH:26]=[C:12]([CH:11]=[C:10]([Cl:29])[C:9]=1[OH:8])[C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=1)=[O:14]

참가 물질

4

반응물 2

HCID 25135Boron TrichlorideHCID 67041711HCID 67041711, 화합물

생성물 1

HCID 4825911Methyl 4-(3,5-dichloro-4-hydroxybenzamido)benzoate수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of methyl 4-(4-(benzyloxy)-3,5-dichlorobenzamido)benzoate (4) (8.8 g, 20.5 mmol) in DCM (500 mL) was cooled to 0° C. and treated dropwise with boron trichloride (20.5 mL, 20.5 mmol, 1 M in DCM). The mixture was then allowed to stir at RT for 12 h. The mixture was cooled in an ice bath then quenched by addition of water (150 mL). The resultant mixture was partitioned between EtOAc (200 mL) and H2O (100 mL). The aqueous phase was extracted with EtOAc (2×75 mL) and the combined organic phases washed successively with water (50 mL) and brine (50 mL), then dried over MgSO4 and filtered. The solvent was removed in vacuo. The residue was crystallised from isohexane/EtOAc to afford methyl 4-(3,5-dichloro-4-hydroxybenzamido)benzoate (5) (5.81 g, 84%): m/z 338 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 11.06 (1H, s), 10.52 (1H, s), 8.06 (2H, s), 8.00 (2H, d), 7.95 (2H, d), 3.88 (3H, s).

후처리

  1. temperatureThe mixture was cooled in an ice bath
  2. customthen quenched by addition of water (150 mL)
  3. customThe resultant mixture was partitioned between EtOAc (200 mL) and H2O (100 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (2×75 mL)
  5. washthe combined organic phases washed successively with water (50 mL) and brine (50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo
  9. customThe residue was crystallised from isohexane/EtOAc

출처 및 근거

ORD 기록
ord-d5eba37f583c45bb9c81c0a1edcdbbdc
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447028B2

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