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

HRID 2173243Notes

Reaction equation

HRID 2173243 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6a79dc60a63c4fa8a86bfe22faec0874
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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