Water → HCID 89524854, compound

HRID 1466035Notes

Reaction equation

HRID 1466035 reaction equation
C[O:2][CH:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]#[N:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.B(Br)(Br)Br.O>C(Cl)Cl>[CH:3]([CH:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]#[N:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86071681HCID 86071681, compound

Product 1

HCID 89524854HCID 89524854, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-(Methoxymethylene)indane-5-carbonitrile (1.5 g, 8.1 mmol) in DCM (40 mL) was added BBr3 (6 g, 24 mmol) at −78° C. The mixture was stirred for 3 hours at −78° C. Then water was added. The mixture was extracted with DCM. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude 1-Formylindane-5-carbonitrile, which was used for next step without further purification. MS m/z: 172 [M+1]+.

Workup

  1. extractionThe mixture was extracted with DCM
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9955efdc5d5045c5acda7f2a9b9d4959
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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