Boron tribromide → 5-Formyl-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

HRID 1466022Notes

Reaction equation

HRID 1466022 reaction equation
C[O:2][CH:3]=[C:4]1[CH2:13][CH2:12][CH2:11][C:10]2[C:9]([C:14]#[N:15])=[CH:8][CH:7]=[CH:6][C:5]1=2.B(Br)(Br)Br>C(Cl)Cl>[CH:3]([CH:4]1[CH2:13][CH2:12][CH2:11][C:10]2[C:9]([C:14]#[N:15])=[CH:8][CH:7]=[CH:6][C:5]1=2)=[O:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 1175993315-(Methoxymethylene)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Product 1

HCID 772306645-Formyl-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(methoxymethylene)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile (320 mg, 1.61 mmol) in DCM (7 mL) was added BBr3 (1.2 g, 4.8 mmol) 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 title compound, which was used for next step.

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-4c5b7f83f37a49f7a01309ba088307a8
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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