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Potassium Phosphate, Tribasic → Methyl (4-(2-hydroxyphenyl)phenyl)acetate

HRID 1757067
Notes
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Reaction equation

HRID 1757067 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[OH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.[Cl-].[Na+].C(OCC)(=O)C>C(COC)OC.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:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 2773454(2-Hydroxyphenyl)boronic acidHCID 86643102Sodium chloride ethyl acetate

Product 1

HCID 54022783Methyl (4-(2-hydroxyphenyl)phenyl)acetateYield 75%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Methyl (4-bromophenyl)acetate (2.79 g, 12.2 mmol), tetrakis(triphenylphosphine)palladium (0) (170 mg), potassium phosphate (9.71 g, 45.75 mmol) and dimethoxyethane (50 ml) were degassed under nitrogen in a 100 ml flask fitted with a reflux condenser. 2-Hydroxybenzene boronic acid (2.52 g, 18.3 mmol) in dimethoxyethane (5 ml) was added and the mixture was heated at reflux overnight then mixed with 1:1 saturated sodium chloride/ethyl acetate (25 ml). The organic materials were separated, dried (MgSO4), then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, gradient hexane to 3:1 hexane/ethyl acetate) which provided 2.21 g (75%) of methyl (4-(2-hydroxyphenyl)phenyl)acetate.

Workup

  1. customfitted with a reflux condenser
  2. temperaturethe mixture was heated
  3. temperatureat reflux overnight
  4. customThe organic materials were separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (SiO2, gradient hexane to 3:1 hexane/ethyl acetate) which

Sources & evidence

ORD record
ord-119d19062c6a4c3493b53a9fdf7b7d7b
Source dataset
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05444050

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes