Boron tribromide → 1-formyl-2,3-dihydro-1H-indene-4-carbonitrile

HRID 1187016ノート

反応式

HRID 1187016 の反応式
C[O:2]/[CH:3]=[C:4]1\[CH2:5][CH2:6][C:7]2[C:8]([C:13]#[N:14])=[CH:9][CH:10]=[CH:11][C:12]\1=2.B(Br)(Br)Br>C(Cl)Cl>[CH:3]([CH:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]#[N:14])[C:7]=2[CH2:6][CH2:5]1)=[O:2]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 68431673(1E)-1-[(methyloxy)methylidene]-2,3-dihydro-1H-indene-4-carbonitrile

生成物 1

HCID 595686981-formyl-2,3-dihydro-1H-indene-4-carbonitrile収率 83.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (1E)-1-[(methyloxy)methylidene]-2,3-dihydro-1H-indene-4-carbonitrile (250 mg, 1.05 mmol) in DCM (5 mL) was added BBr3 dropwise at −78° C. under N2. Then the mixture was stirred at this temperature for 3 h. It was poured into ice-saturated NaHCO3 solution, and extracted with DCM. The organic layer was washed with brine and dried over Na2SO4. The solvent was removed in vacuo to give crude 1-formyl-2,3-dihydro-1H-indene-4-carbonitrile (150 mg, crude), which is used for next step directly.

後処理

  1. additionIt was poured into ice-saturated NaHCO3 solution
  2. extractionextracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-d0299106a2694f41935becdd71d9f814
出典データセット
uspto-grants-2014_03
特許番号
US08673920B2

反応ノート

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