Water → HCID 57827655, compound

HRID 1842102Notes

Reaction equation

HRID 1842102 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].[Cl-].[NH4+:15].[OH2:16].[O:17]1CCCC1.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCCCCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:26]([C@@H:27]1[C@@H:22]2[C@@:23]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[F:13])([NH:15][O:17][CH2:28]2)[CH2:24][O:16]1)[CH3:25]

Participants

9

Reactant 5

HCID 962WaterHCID 25517Ammonium ChlorideHCID 612591-Bromo-2-fluorobenzeneHCID 22635083Tetrahydrofuran tolueneHCID 178418339Butyllithium

Product 1

HCID 57827655HCID 57827655, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of n-butyllithium in hexane (2.60 M; 12.2 mL) was added dropwise to a solution containing 2-bromofluorobenzene (3.62 mL) in tetrahydrofuran/toluene (5.80 mL/58.0 mL) under a nitrogen atmosphere at −78° C. The reaction solution was stirred at the same temperature for 10 minutes. A boron trifluoride-diethyl ether complex (3.92 mL) and a solution containing the compound obtained in Preparation Example 21-(2) (2.02 g) in toluene (20 mL) were added dropwise to the reaction solution sequentially at the same temperature. After stirring at the same temperature for 40 minutes, aqueous ammonium chloride was added to the reaction solution, followed by warming to room temperature. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with a saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the insoluble matter was separated by filtration. The filtrate was concentrated and the residue was purified by silica gel column chromatography to obtain the title compound (3.39 g).

Workup

  1. additionA boron trifluoride-diethyl ether complex (3.92 mL) and a solution containing the compound
  2. additionwere added dropwise to the reaction solution sequentially at the same temperature
  3. stirringAfter stirring at the same temperature for 40 minutes
  4. customthe organic layer was separated
  5. washThe organic layer was washed with a saturated sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe insoluble matter was separated by filtration
  8. concentrationThe filtrate was concentrated
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6a9dd394eeb7408d98474cd3e6de46a3
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

Loading…