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Ethanol → HCID 67343100, compound

HRID 1673474
Notes
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Reaction equation

HRID 1673474 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.C(=O)([O-])O.[Na+].C(O)C.[C:18]([NH:26][C:27]1[CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH:37]=[CH:36][C:28]=1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.O>[C:18]([NH:26][C:27]1[CH:39]=[C:38]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=2)[CH:37]=[CH:36][C:28]=1[C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 702EthanolHCID 198594-Bromo-2-chlorophenolHCID 516892Sodium Bicarbonate2×HCID 67342196HCID 67342196, compound

Product 1

HCID 67343100HCID 67343100, compound

Reagents, catalysts & solvents 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent2×

Procedure

0.15 g of 4-bromo-2-chlorophenol, 0.18 g of sodium hydrogen carbonate, 0.6 mL of ethanol, 0.3 mL of water and 42 mg of tetrakis(triphenylphosphine) palladium(0) were added to 2.1 mL of toluene solution containing 0.37 g of tert-butyl 2-(benzamido)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate at room temperature, and the resulting mixture was heated to reflux for 4 hours. Toluene and a saturated sodium hydrogen carbonate aqueous solution were added after the reaction mixture was cooled to room temperature. The organic layer was separated and ethyl acetate was added after washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane was added to the obtained residue and a solid substance was separated by filtration to obtain tert-butyl 2-(benzamido)-4-(3-chloro-4-hydroxyphenyl)benzoate.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe organic layer was separated
  4. additionethyl acetate was added
  5. washafter washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. additionHexane was added to the obtained residue
  9. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-e4cc7abcc9354b6b867ad613b2a57ccb
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07999132B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes