Triethylamine → 1-Fluoro-4-methyl-2-phenoxybenzene

HRID 1371968Notes

Reaction equation

HRID 1371968 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[OH:16].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)Cl>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 182387Phenol, 2-fluoro-5-methyl-

Product 1

HCID 142572981-Fluoro-4-methyl-2-phenoxybenzeneYield 29%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Add triethylamine (28.6 mL, 205 mmol) dropwise to a mixture of 2-fluoro-5-methylphenol (5.18 g, 41.1 mmol), copper(II) acetate (7.46 g, 41.1 mmol), phenylboronic acid (10.0 g, 82.1 mmol), powdered 4 Å sieves (7 g), and methylene chloride (400 mL). Stir at ambient temperature. After 22 h, filter and concentrate the filtrate. Purify the residue by silica gel chromatography (50% methylene chloride/hexanes), concentrate and purify again by silica gel chromatography (100% hexanes) to give 2.4 g (29%) of the title compound: MS(m/e): 202 (M+).

Workup

  1. filtrationfilter
  2. concentrationconcentrate the filtrate
  3. customPurify the residue by silica gel chromatography (50% methylene chloride/hexanes)
  4. concentrationconcentrate
  5. custompurify again by silica gel chromatography (100% hexanes)

Sources & evidence

ORD record
ord-b742d4ee4d8748ec87397285d417643a
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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