4-Chlorophenylboronic acid → HCID 10641092, compound

HRID 1839929Notes

Reaction equation

HRID 1839929 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 10710131HCID 10710131, compound

Product 1

HCID 10641092HCID 10641092, compoundYield 74.9%

Procedure

Following the general procedure outlined in Synthetic Scheme VI, 2.3 g (7.4 mmol) of 1-bromo-2-[4-(methylsulfonyl)phenyl]benzene (Example 4, Step 2) was reacted with 1.7 g (11 mmol) of 4-chlorophenylboronic acid. Purification by silica gel chromatography (Waters Prep-500A) with ethyl acetate/hexane (1:3) and subsequent recrystallization from ethyl acetate/hexane gave 1.90 g (74%) of 1-(4-chlorophenyl)-2-[4-(methylsulfonyl)phenyl]benzene as a colorless solid: mp 180.2-180.6° C.; NMR (CDCl3) δ 3.06 (s, 3H), 7.04 (d, J=8 Hz, 2H), 7.21 (d, J=8 Hz, 2H), 7.33 (d, J=9 Hz, 2H), 7.38-7.51 (m, 4H), 7.81 (d, J=8 Hz, 2H). MS (EI): m/e (rel intensity) 342 (34), 228 (100); HRMS Calc'd for C19H15ClO2S: 342.0481. Found: 342.0484. Anal. Calc'd for C19H15ClO2S: C, 66.56; H, 4.41; Cl, 10.34. Found: C, 66.45; H, 4.48; Cl, 10.63.

Workup

  1. customPurification by silica gel chromatography (Waters Prep-500A)
  2. customwith ethyl acetate/hexane (1:3) and subsequent recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-cde1c9b89aa94837999319b583be82c0
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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