Potassium Carbonate → HCID 68544738, compound

HRID 2384015Notes

Reaction equation

HRID 2384015 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[C:4]([OH:13])[C:3]=1[F:14].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>CN(C)C=O>[C:26]([O:25][C:23](=[O:24])[CH2:22][O:13][C:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=[C:2]([Cl:1])[C:3]=1[F:14])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 59192513HCID 59192513, compound

Product 1

HCID 68544738HCID 68544738, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7-chloro-6-fluoro-5-hydroxy-3,4-dihydro-2H-naphthalen-1-one (0.90 g, 4.18 mmol) in dry N,N-dimethylformamide (10 mL) was added potassium carbonate (1.16 g, 8.36 mmol) and tert-butyl bromoacetate (1.22 g, 6.27 mmol) at room temperature and the resulting mixture was stirred for 2 hours, then extracted with ethyl acetate (25 mL×3), washed with water (25 mL×3), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford (3-chloro-2-fluoro-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (1.32 g, 96%), which was used in the next step without further purification. MS cald. for C16H18ClFO4 328, obsd. 329 [(M+H)+].

Workup

  1. extractionextracted with ethyl acetate (25 mL×3)
  2. washwashed with water (25 mL×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a1c621e98204e7c85725dfa4d5f666d
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

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