Hydrochloric Acid → HCID 86707576, compound

HRID 2279970Notes

Reaction equation

HRID 2279970 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][O:19][C:20](=[O:31])[CH:21]=[CH:22][C:23]1[CH:28]=[C:27](Br)[CH:26]=[C:25](Br)[CH:24]=1.Cl>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:18][O:19][C:20](=[O:31])/[CH:21]=[CH:22]/[C:23]1[CH:28]=[C:27]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[CH:26]=[C:25]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[CH:24]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 27343144-Benzyloxy-phenylboronic acidHCID 69906829HCID 69906829, compound

Product 1

HCID 86707576HCID 86707576, compound

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.00 g (14.4 mmol) sodium metaborate-octahydrate and 250 mg (0.349 mmol) bis(triphenylphosphine)palladium(II)chloride are stirred for 15 min in 50 ml THF and 50 ml water, and 5.00 g (21.3 mmol) 4-benzyloxybenzene boronic acid, 3.00 g (9.37 mmol) 3,5-dibromo cinnamic acid methyl ester are added and the mixture is stirred overnight at reflux. The mixture is acidified with 2 M hydrochloric acid, the precipitated product is filtered off, suspended in hot ethanol, filtered off and used in the next step without further purification.

Workup

  1. temperatureat reflux
  2. filtrationthe precipitated product is filtered off
  3. filtrationfiltered off
  4. customused in the next step without further purification

Sources & evidence

ORD record
ord-d868a1a3a1b1463fa9fe7431ce2c386c
Source dataset
uspto-grants-2015_09
Patent number
US09133395B2

Reaction notes

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