2-Bromophenol → HCID 22046255, compound

HRID 1830501Notes

Reaction equation

HRID 1830501 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[C:9]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.C(N(CC)CC)C>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:21]1[CH:22]=[CH:23][C:18]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 72442-BromophenolHCID 8471TriethylamineHCID 1512531,1'-Biphenyl-4-yl-boronic acid

Product 1

HCID 22046255HCID 22046255, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-bromophenol (2.08 g, 12 mmol), 4-biphenylboronic acid (4.75 g, 24 mmol), Cu(OAc)2 (2.20 g, 12 mmol) and triethylamine (6.1 g, 60 mmol) in dioxane (100 mL) was stirred for 48 h. The crude mixture was evaporated onto silica gel and purified by column chromatography eluting with ethyl acetate/heptane 1:9. Yield: 0.73 g (19%). 1H NMR (CDCl3, 500 MHz) 7.65 (m, 1H) 7.55 (m, 4H), 7.43 (m, 2H), 7.25–7.38 (m, 2H), 7.00–7.08 (m, 4H); MS(m/z): 325.1.

Workup

  1. customThe crude mixture was evaporated onto silica gel
  2. custompurified by column chromatography
  3. washeluting with ethyl acetate/heptane 1:9

Sources & evidence

ORD record
ord-e9fc694eb9514f36aa3bb37243bc0c2a
Source dataset
uspto-grants-2006_06
Patent number
US07067501B2

Reaction notes

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