3-Benzyloxy-phenylboronic acid → HCID 66931060, compound

HRID 511986Notes

Reaction equation

HRID 511986 reaction equation
COC([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](OCC3C=CC=CC=3)[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=O.[CH3:25][O:26][C:27](=[O:36])[CH2:28]C1C=CC=C(Br)C=1.[CH2:37]([O:44]C1C=C(B(O)O)C=CC=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[OH-].[Ba+2].[OH-]>COCCOC.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.O>[CH3:25][O:26][C:27](=[O:36])[CH2:28][C:13]1([O:44][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:14]=[CH:15][CH:16]=[C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:5][CH:6]=2)[CH2:12]1

Participants

8

Reactant 4

HCID 27343133-Benzyloxy-phenylboronic acidHCID 6093286Barium hydroxideHCID 11746402Methyl 2-(3-bromophenyl)acetateHCID 20099919HCID 20099919, compound

Product 1

HCID 66931060HCID 66931060, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-(3-Benzyloxy-biphenyl-3-yl)-acetic acid methyl ester (32) was synthesized following the procedure described for the preparation of 29 using 3-bromo-phenyl acetic acid methyl ester (31) (0.31 g, 1.35 mmol), 3-benzyloxy-phenyl boronic acid (0.45 g, 2 mmol), barium hydroxide (0.5 g, 3 mmol) and Pd(PPh3)4 (0.15 g, 0.13 mmol), in DME (10 mL)/water (4 mL). Purification by flash column chromatography on silica gel gave pure compound 32 (0.22 g, 49% yield) as a white solid (m p 50-52° C.).

Workup

  1. custom2-(3-Benzyloxy-biphenyl-3-yl)-acetic acid methyl ester (32) was synthesized
  2. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-a90ef4f486714223ad3fc6a39a87284b
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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