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

HRID 2173243ノート

反応式

HRID 2173243 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

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, which is used for next step directly. 1H-NMR (400 MHz, CDCl3) δ ppm 9.72 (s, 1H), 7.54 (d, J=7.6 Hz, 2H), 7.34 (t, J=7.6 Hz, 1H), 3.76 (s, 1H), 3.18-3.24 (m, 2H), 2.42-2.58 (m, 2H).

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-6a79dc60a63c4fa8a86bfe22faec0874
出典データセット
uspto-grants-2015_06
特許番号
US09056859B2

反応ノート

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