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Potassium Carbonate → Methyl 3-benzyloxy-5-phenylbenzoate

HRID 1431001
Notes
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Reaction equation

HRID 1431001 reaction equation
C1COCC1.O.[CH3:7][O:8][C:9](=[O:32])[C:10]1[CH:15]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:13]=[C:12]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:11]=1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C.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>[CH3:7][O:8][C:9]([C:10]1[CH:15]=[C:14]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:13]=[C:12]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:11]=1)=[O:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 18945283Methyl 3-benzyloxy-5-(trifluoromethanesulfonyloxy)benzoateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 18945315Methyl 3-benzyloxy-5-phenylbenzoateYield 90.8%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 3283Diethyl EtherSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of THF/H2O (5 mL, v/v=4:1) in a microwave vial was added 3-benzyloxy-5-trifluoromethanesulfonyloxy-benzoic acid methyl ester (100 mg, 0.256 mmol), phenylboronic acid (34 mg, 0.281 mmol), potassium carbonate (71 mg, 0.512 mmol), and Pd(PPh3)4 (15 mg, 0.02 mmol). The reaction vessel was sealed and subjected to microwave heating for 5 min at 130° C. After cooling, it was diluted with diethyl ether and washed with brine, dried (MgSO4), and evaporated. The residue was subjected to chromatography on silica gel using an ethyl acetate-hexane gradient to afford 74 mg (90%) of 5-benzyloxybiphenyl-3-carboxylic acid methyl ester: LCMS m/z=319.4 [C21H18O3+H]+.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-792c66f82eed4a06b8ff532e1d0997ab
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08940927B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes