Ethyl Acetate → HCID 58543873, compound

HRID 1921573Notes

Reaction equation

HRID 1921573 reaction equation
[Br:1][CH2:2][C:3]([C:25]([F:28])([F:27])[F:26])([OH:24])[CH:4]([NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]C)[CH:6]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl>[Br:1][CH2:2][C:3]([C:25]([F:26])([F:27])[F:28])([OH:24])[CH:4]([NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 58543833HCID 58543833, compound

Product 1

HCID 58543873HCID 58543873, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 20 mg (0.04 mmol) of α-Bromomethyl-3-methoxy-β-[(naphth-1-yl)amino]-α-(trifluoromethyl)benzeneethanol in 2 ml dichloromethane at −20° C. are added 0.44 ml of a 1 M solution of boron tribromide in dichloromethane under argon. The reaction mixture is stirred for 16 hours in a temperature range of between 0° C. and 25° C. The reaction mixture is mixed at 0° C. with saturated sodium bicarbonate solution. After dilution with ethyl acetate the batch is allowed to come to room temperature, stirred for 10 minutes and extracted twice with ethyl acetate. The combined organic extracts are washed with saturated NaCl solution and dried over sodium sulfate. The solvent is evaporated and the residue purified by preparative thin layer chromatography on silica gel (ethyl acetate in hexane 33%). 6.5 mg of the desired compound are isolated.

Workup

  1. customto come to room temperature
  2. stirringstirred for 10 minutes
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts are washed with saturated NaCl solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is evaporated
  7. customthe residue purified by preparative thin layer chromatography on silica gel (ethyl acetate in hexane 33%)

Sources & evidence

ORD record
ord-2e35ecbfbbf04c328bd06857416418ca
Source dataset
uspto-grants-2012_05
Patent number
US08173676B2

Reaction notes

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