Bromine → 6-Bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1436074Notes

Reaction equation

HRID 1436074 reaction equation
[Br:1]Br.[O:3]=[C:4]1[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([C:14]#[N:15])[CH:7]=[CH:6][C:5]1=2>C(Cl)Cl>[Br:1][CH:13]1[CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([C:14]#[N:15])[CH:7]=[CH:6][C:5]=2[C:4]1=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 108991325-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 675113086-Bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrileYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bromine (0.8 mL, 15.7 mmol) was added to a solution of 5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile (2.7 g, 15.7 mmol), prepared in the previous step, in dry methylene chloride (55 mL) at 0° C. The reaction was warmed to room temperature. After 2 h, the reaction was diluted with methylene chloride and washed with 5% sodium thiosulfate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 4.3 g of crude product. Purification of the crude product on silica gel using 10% ethyl acetate:hexane as the eluent gave 6-bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (3.2 g, 81%), MS(ES) m/z 251 [M+H]+.

Workup

  1. washwashed with 5% sodium thiosulfate and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give 4.3 g of crude product
  6. customPurification of the crude product on silica gel using 10% ethyl acetate

Sources & evidence

ORD record
ord-c818885d78b04921a02d5db85e5e0bc8
Source dataset
uspto-grants-2009_11
Patent number
US07618989B2

Reaction notes

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