1-Butanol → HCID 90229418, compound

HRID 1505752Notes

Reaction equation

HRID 1505752 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8](F)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12]([OH:16])[CH2:13][CH2:14][CH3:15].CC(C)([O-])C.[K+].Cl>C1COCC1.CN(C=O)C.O>[CH2:12]([O:16][C:8]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])[CH2:13][CH2:14][CH3:15]

Participants

8

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 3028882-Chloro-5-fluorobenzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 90229418HCID 90229418, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-5-fluorobenzoic acid (50 mg) and 1-butanol (263 μL) in THF (0.5 mL) and DMF (3 mL) was added potassium t-butoxide (329 mg) and the solution was reacted at 120° C. for 10 minutes in a microwave synthesizer (Biotage, Initiator). The reaction mixture was cooled and acidified by addition of water and 2M hydrochloric acid, extracted with diethyl ether, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified on column chromatography to obtain the titled compound (17 mg) as white powder.

Workup

  1. customthe solution was reacted at 120° C. for 10 minutes in a microwave synthesizer (Biotage, Initiator)
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with diethyl ether
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified on column chromatography

Sources & evidence

ORD record
ord-bd5de2f9bd484c2dbcf3605a28c93fba
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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