Potassium Carbonate → Tert-butyl 5-chloro-4-((2,2-dimethylchroman-7-yloxy)methyl)-2-fluorobenzoate

HRID 1849521Notes

Reaction equation

HRID 1849521 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[O:3]1.Br[CH2:15][C:16]1[C:28]([Cl:29])=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[C:18]([F:30])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:29][C:28]1[C:16]([CH2:15][O:12][C:6]2[CH:5]=[C:4]3[C:9]([CH2:10][CH2:11][C:2]([CH3:13])([CH3:1])[O:3]3)=[CH:8][CH:7]=2)=[CH:17][C:18]([F:30])=[C:19]([CH:27]=1)[C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110412812,2-dimethyl-3,4-dihydro-2H-1-benzopyran-7-olHCID 86702928HCID 86702928, compound

Product 1

HCID 86702867Tert-butyl 5-chloro-4-((2,2-dimethylchroman-7-yloxy)methyl)-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2,2-dimethylchroman-7-ol (100 mg, 0.561 mmol), tert-butyl 4-(bromomethyl)-5-chloro-2-fluorobenzoate (191 mg, 0.590 mmol) and potassium carbonate (194 mg, 1.40 mmol) in acetone (30 mL) was stirred at 50° C. for 16 hrs. After cooling to room temperature, the mixture was extracted with EtOAc (150×5 mL). The combined orgaic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product which was used in next step without further purification (290 mg, crude). LCMS (ESI) m/z: 420.8 [M+H].

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc (150×5 mL)
  3. washThe combined orgaic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-931b74e83ade41afb5978745ec36b14b
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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