HCID 89676556, compound → HCID 89676548, compound

HRID 926223Notes

Reaction equation

HRID 926223 reaction equation
[Br:1][C:2]1(Br)[CH:11]([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[C:3]1=[O:14].N1(C2CCCCCCCCCC2)CCCN=CCCCCC1>CC#N>[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[C:3]=1[OH:14]

Participants

4

Reactant 2

HCID 89676556HCID 89676556, compoundHCID 1296629601,8-Diazabicycloundec-7ene

Product 1

HCID 89676548HCID 89676548, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2,2-dibromo-3,6-dimethyl-3,4-dihydronaphthalen-1(2H)-one (61.2 g, 184 mmol) in MeCN (1.5 L) was cooled to −40° C. internal temperature using a dry ice/acetone bath. 1,8-Diazabicycloundec-7-ene (41.6 mL, 279 mmol) was added as a solution in MeCN (150 mL) and the reaction was allowed to warm to room temperature overnight. The majority of the reaction solvent was removed in vacuo and the residue taken up in EtOAc (1 L) and washed with 0.5 M HCl (1 L). The resulting aqueous layer was extracted with several portions of EtOAc and the combined organics were washed with brine. Following drying over anhydrous MgSO4 and concentration in vacuo, the resulting residue was absorbed directly onto 200 g silica gel and eluted on Isco silica gel column chromatography (0-20% EtOAc/hex) to afford 2-bromo-3,6-dimethylnaphthalen-1-ol. LCMS-ESI+ (m/z): [M]+ calcd for C12H11BrO: 251.1. found: 251.4.

Workup

  1. customThe majority of the reaction solvent was removed in vacuo
  2. washwashed with 0.5 M HCl (1 L)
  3. extractionThe resulting aqueous layer was extracted with several portions of EtOAc
  4. washthe combined organics were washed with brine
  5. dry with materialFollowing drying over anhydrous MgSO4 and concentration in vacuo
  6. customthe resulting residue was absorbed directly onto 200 g silica gel
  7. washeluted on Isco silica gel column chromatography (0-20% EtOAc/hex)

Sources & evidence

ORD record
ord-767ca44edcf74027b90df77ac91b5524
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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