P-Chloroacetophenone → HCID 86722002, compound

HRID 1398035Notes

Reaction equation

HRID 1398035 reaction equation
N1([C:10]([CH:12]2[CH2:17][C:16]([CH3:19])([CH3:18])[O:15][C:14]([CH3:21])([CH3:20])[CH2:13]2)=[O:11])C2C=CC=CC=2N=N1.CCOCC.[Mg+2].[Br-].[Br-].[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37](=[O:39])[CH3:38])=[CH:33][CH:32]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37](=[O:39])[CH2:38][C:10]([CH:12]2[CH2:13][C:14]([CH3:20])([CH3:21])[O:15][C:16]([CH3:18])([CH3:19])[CH2:17]2)=[O:11])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 7467P-ChloroacetophenoneHCID 81531DiisopropylethylamineHCID 9903262Magnesium bromide diethyl etherateHCID 86721999Benzotriazol-1-yl-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-methanone

Product 1

HCID 86722002HCID 86722002, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of benzotriazol-1-yl-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-methanone (1.00 g, 3.13 mmol), magnesium bromide diethyl etherate (1.62 g, 6.26 mmol), and 1-(4-chloro-phenyl)-ethanone (0.39 mL, 2.98 mmol) in 10 mL of DCM at RT was added dropwise DIEA (1.74 mL, 9.40 mmol). The mixture was stirred overnight and then diluted with 50 mL of DCM and washed with 1N HCl (100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, concentrated, and the residue purified by flash chromatography on silica gel to give 0.70 g (69%) of a white solid.

Workup

  1. washwashed with 1N HCl (100 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customthe residue purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-33d2cb65b6894f3d8a26da99d60e20ab
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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