2,6-Lutidine → HCID 86700769, compound

HRID 2406504Notes

Reaction equation

HRID 2406504 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Br:16][C:17]1[C:25](O)=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][CH2:20][C:21]2=[O:27].CC1C=CC=C(C)N=1>ClCCl>[Br:16][C:17]1[C:25]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][CH2:20][C:21]2=[O:27]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 688667904-Bromo-5-hydroxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 86700769HCID 86700769, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoromethanesulfonic anhydride (4.0 mL) is added dropwise to a solution of 4-bromo-5-hydroxy-indan-1-one (5.0 g) and 2,6-dimethylpyridine (5.1 mL) in dichloromethane (50 mL) cooled to 0° C. The cooling bath is removed and the mixture is stirred for 2 h at room temperature. The solution is partitioned between saturated aqueous NH4Cl solution and dichloromethane. The organic phase is separated, washed with brine, dried (MgSO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50) to give the title compound. LC (method 2): tR=1.08 min; Mass spectrum (ESI+): m/z=359/361 (Br) [M+H]+.

Workup

  1. customThe cooling bath is removed
  2. customThe solution is partitioned between saturated aqueous NH4Cl solution and dichloromethane
  3. customThe organic phase is separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50)

Sources & evidence

ORD record
ord-d7bff5d43bf64878b974949346eeaae3
Source dataset
uspto-grants-2014_08
Patent number
US08809376B2

Reaction notes

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