Boron tribromide → HCID 71185821、化合物

HRID 1470512ノート

反応式

HRID 1470512 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:9][CH:8]=[C:7]2[O:17]C.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([N:14]([CH3:15])[CH3:16])=[O:13])=[CH:9][CH:8]=[C:7]2[OH:17]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 71186206HCID 71186206、化合物

生成物 1

HCID 71185821HCID 71185821、化合物収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

8-chloro-4-methoxy-N,N-dimethyl-1-naphthamide (step-5 intermediate) (0.5 g, 1.90 mmol) in DCM (15 mL) was cooled to −78° C. Then, BBr3 (0.72 mL, 7.58 mmol) in DCM (7.5 mL) was added dropwise to the mixture at −78° C. The reaction mixture was warmed to RT and stirred for 2 h, and quenched with brine solution. The aqueous layer was extracted with DCM, and the combined organic layer was washed with, water, brine, dried over Na2SO4 and filtered. The solvent was evaporated to provide the desired phenol as pale brown solid (445 mg, 94%) that was used in next step without any further purification.

後処理

  1. customquenched with brine solution
  2. extractionThe aqueous layer was extracted with DCM
  3. washthe combined organic layer was washed with, water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-dd344b96f65a42fd983069e3d32c16d1
出典データセット
uspto-grants-2015_04
特許番号
US09006442B2

反応ノート

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