Triethylamine → HCID 21454544, compound

HRID 1057165Notes

Reaction equation

HRID 1057165 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[Cl:16].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC([O-])=O.CC([O-])=O.[Cu+2].ClCCl>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[Cl:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic Acid2×HCID 70181824-Bromo-3-chlorophenol

Product 1

HCID 21454544HCID 21454544, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.52 mL, 3.75 mmol) was added to a mixture of 4-bromo-3-chlorophenol (156 mg, 0.75 mmol), phenyl boronic acid (187 mg, 1.53 mmol), Cu(OAc)2 (208 mg, 1.15 mmol), molecular sieves (4 Å), and dichloromethane (7.5 mL). The mixture was stirred at room temperature overnight, and then additional phenyl boronic acid (186, 1.53 mmol) was added. The reaction was stirred at rt for an additional 7 h and filtered through Celite with dichloromethane. The filtrate was concentrated and purified by silica gel chromatography (100% hexanes) to give 1-bromo-2-chloro-4-phenoxybenzene (90 mg) as a clear liquid. 1H NMR (400 MHz, DMSO-d6): δ 7.75 (d, 1H), 7.42-7.47 (m, 2H), 7.27 (d, 1H), 7.23 (t, 1H), 7.11 (d, 2H), 6.92 (dd, 1H).

Workup

  1. stirringThe reaction was stirred at rt for an additional 7 h
  2. filtrationfiltered through Celite with dichloromethane
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel chromatography (100% hexanes)

Sources & evidence

ORD record
ord-11ae883c85b3429190250ccca941df2b
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

Loading…