Benzyl Bromide → HCID 66611362, compound

HRID 2204708Notes

Reaction equation

HRID 2204708 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([C:19]([F:22])([F:21])[F:20])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(OCC)(=O)C>CN(C)C=O.O>[C:30]1([CH2:29][O:1][C:2]2[CH:11]=[C:10]([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:9]([C:19]([F:22])([F:20])[F:21])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 66611811HCID 66611811, compound

Product 1

HCID 66611362HCID 66611362, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 2-hydroxy-4-(1-piperidinylmethyl)-5-(trifluoromethyl)benzoate (may be prepared as described in Description 51; 230 mg, 0.72 mmol) was dissolved in N,N-dimethylformamide (5 mL) and cesium carbonate (264 mg, 0.81 mmol) and benzyl bromide (0.12 ml, 1.01 mmol) were added. The mixture was heated at 40° C. for 18 hours. Ethyl acetate (10 ml) and water (10 ml) were added and the organic layer was separated and washed with water (2×10 ml), dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (1:1 cyclohexane/ethyl acetate-10% 7M NH3 in methanol/dichloromethane) gave the title compound as oil. 232 mg.

Workup

  1. customthe organic layer was separated
  2. washwashed with water (2×10 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customPurification by column chromatography (1:1 cyclohexane/ethyl acetate-10% 7M NH3 in methanol/dichloromethane)

Sources & evidence

ORD record
ord-1eca90439bae4bdaa977fe65334a61f4
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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