Hydrochloric Acid → Methyl 4-(3-hydroxyphenyl)benzoate

HRID 393288Notes

Reaction equation

HRID 393288 reaction equation
[C:1]([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.B([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(O)O.Cl>CC#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:14][C:10]1[CH:9]=[C:8]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([O:24][CH3:1])=[O:23])=[CH:20][CH:19]=2)[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 115633-BromophenolHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 4564855Methyl 4-(3-hydroxyphenyl)benzoateYield 57%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

An aqueous 0.4 M Na2CO3 solution (21.7 mL) was added to a solution of 3-bromophenol (500 mg, 2.89 mmol) and 4-boronobenzoic acid (480 mg, 2.89 mmol) in MeCN (14.5 mL). The mixture was degassed with argon (10 min) then Pd(PPh3)4 (168 mg, 0.14 mmol) was added. The reaction mixture was heated to 90° C. for 12 h. The cooled mixture was acidified with aqueous 1 N HCl solution and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. A solution of the residue in Et2O (150 mL) was treated with excess ethereal CH2N2 solution (ca. 0.6 M) then was concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 85:15) to give the title compound (375 mg, 57% yield) as a yellow solid.

Workup

  1. customThe mixture was degassed with argon (10 min)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionA solution of the residue in Et2O (150 mL) was treated with excess ethereal CH2N2 solution (ca. 0.6 M)
  8. concentrationthen was concentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (Hexane:EtOAc, 85:15)

Sources & evidence

ORD record
ord-a3eb97ab68e34f9ca3e6fa660419cdee
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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