3-Chloro-4-methoxybenzeneboronic acid → HCID 10667040, compound

HRID 1839928Notes

Reaction equation

HRID 1839928 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:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]>>[Cl:18][C:19]1[CH:20]=[C:21]([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:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

3

Reactant 2

HCID 32475223-Chloro-4-methoxybenzeneboronic acidHCID 10710131HCID 10710131, compound

Product 1

HCID 10667040HCID 10667040, compoundYield 69%

Procedure

Following the general procedure outlined in Synthetic Scheme VI, 4.0 g (13 mmol) of 1-bromo-2-[4-(methylsulfonyl)phenyl]benzene (Example 4, Step 2) was reacted with 2.86 g (15.4 mmol) of 3-chloro-4-methoxyphenylboronic acid (Step 2). Purification by silica gel chromatography (Waters PrepLC500A) with ethyl acetate/hexane (35:65) and subsequent recrystallization from ethyl acetate/hexane gave 3.31 g (69%) of 2-chloro-1-methoxy-4-[2-[4-(methylsulfonyl)phenyl]phenyl]benzene as a colorless solid: mp 161.5-162.3° C.; NMR (CDCl3) δ 3.05 (s, 3H), 3.88 (s, 3H), 6.75 (d, J=9 Hz, 1H), 6.87 (dd, J=1.5, 9 Hz, 1H), 7.17 (d, J=2 Hz, 1H), 7.34 (d, J=9 Hz, 2H), 7.37-7.51 (m, 4H), 7.82 (d, J=8 Hz, 2H). MS (EI): m/e (rel intensity) 372 (100), 243 (24); HRMS Calc'd for C20H17ClO3S: 372.0587. Found: 372.0557. Anal. Calc'd for C20H17ClO3S: C, 64.43; H, 4.60; Cl, 9.51. Found: C, 64.17; H, 4.56; Cl, 9.63.

Workup

  1. customPurification by silica gel chromatography (Waters PrepLC500A)
  2. customwith ethyl acetate/hexane (35:65) and subsequent recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-104a391a83e84af99ad8b4057e576a1d
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

Loading…