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

HRID 62716ノート

反応式

HRID 62716 の反応式
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]

参加物

4

反応物 2

HCID 25135Boron TrichlorideHCID 67041711HCID 67041711、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d5eba37f583c45bb9c81c0a1edcdbbdc
出典データセット
uspto-grants-2016_09
特許番号
US09447028B2

反応ノート

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