Boron tribromide → 5-Fluoro-1-formyl-2,3-dihydro-1H-indene-4-carbonitrile

HRID 2173246Notes

Reaction equation

HRID 2173246 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[C:7](=[CH:11][O:12]C)[CH2:6][CH2:5][C:4]=2[C:3]=1[C:14]#[N:15].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[CH:7]([CH:11]=[O:12])[CH2:6][CH2:5][C:4]=2[C:3]=1[C:14]#[N:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 1317329685-Fluoro-1-(methoxymethylidene)-2,3-dihydro-1H-indene-4-carbonitrile

Product 1

HCID 874299245-Fluoro-1-formyl-2,3-dihydro-1H-indene-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-Fluoro-1-(methoxymethylidene)-2,3-dihydro-1H-indene-4-carbonitrile (10 mg, 0.049 mmol) in DCM was cooled to −78° C. To this solution was dropped BBr3 (0.492 ml, 0.492 mmol). The mixture was allowed to stir for 15 minutes, and then it was diluted with DCM (10 mL), washed with NaHCO3, dried over Na2SO4, and concentrated. The residue was used directly in the next step.

Workup

  1. washwashed with NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-143e9385c53848ee82ac728f05bd2691
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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