Potassium Carbonate → Tert-butyl 5-chloro-4-((7,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)methyl)-2-fluorobenzoate

HRID 1849591Notes

Reaction equation

HRID 1849591 reaction equation
Br[CH2:2][C:3]1[C:15]([Cl:16])=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([F:17])[CH:4]=1.[CH3:18][C:19]1([CH3:30])[CH2:28][C:27]2[CH:26]=[C:25]([OH:29])[CH:24]=[CH:23][C:22]=2[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:16][C:15]1[C:3]([CH2:2][O:29][C:25]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][C:19]([CH3:30])([CH3:18])[CH2:28][C:27]=3[CH:26]=2)=[CH:4][C:5]([F:17])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86702928HCID 86702928, compoundHCID 867029297,7-Dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 86702927Tert-butyl 5-chloro-4-((7,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)methyl)-2-fluorobenzoateYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of tert-butyl 4-(bromomethyl)-5-chloro-2-fluorobenzoate (200 mg, 0.62 mmol), 7,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol (109 mg, 0.62 mmol) and potassium carbonate (257 mg, 1.86 mmol) in acetone (20 mL) was stirred at 50° C. for 4 hrs. The reaction mixture was filtered, the filtrate was concentrated and purified by SGC (eluting with petroleum ether/ethyl acetate from 100/1 to 25/1) to get the desired compound (220 mg, 85%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified by SGC (eluting with petroleum ether/ethyl acetate from 100/1 to 25/1)

Sources & evidence

ORD record
ord-61add4976d854bcb81d3adc0847e48f6
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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