Water → HCID 57827762, compound

HRID 1842104Notes

Reaction equation

HRID 1842104 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].[Cl-].[NH4+:15].[OH2:16].[O:17]1CC[CH2:19][CH2:18]1.C1(C)C=CC=CC=1>CCCCCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C@:3]12[CH2:4][O:17][C@H:18]([CH3:19])[C@H:2]1[CH2:1][O:16][NH:15]2

Participants

9

Reactant 5

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

Product 1

HCID 57827762HCID 57827762, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of n-butyllithium in hexane (2.60 M; 6.05 mL) was added dropwise to a solution containing 2-bromofluorobenzene (1.79 mL) in tetrahydrofuran/toluene (2.88 mL/28.8 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 (1.94 mL) and a solution containing the compound obtained in Preparation Example 22-(2) (1.00 g) in toluene (10 mL) were added dropwise to the reaction solution sequentially at the same temperature. After stirring at the same temperature for one hour, aqueous ammonium chloride was added to the reaction solution, and the reaction solution was warmed 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 (1.60 g). ESI-MS; m/z 224 [M++H].

Workup

  1. additionA boron trifluoride-diethyl ether complex (1.94 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 one hour
  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-125676a3c9e748dbaf5c14964c5b453e
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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