3-Chlorophenylboronic acid ethylene glycol ester → (3-Chlorophenyl)(3,4-dimethoxyphenyl)borinic acid

HRID 746478Notes

Reaction equation

HRID 746478 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[B:13](OCCO)([OH:21])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1>>[Cl:20][C:16]1[CH:15]=[C:14]([B:13]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[OH:21])[CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 692083603-Chlorophenylboronic acid ethylene glycol esterHCID 178491916HCID 178491916, compound

Product 1

HCID 69207503(3-Chlorophenyl)(3,4-dimethoxyphenyl)borinic acid

Procedure

(3-Chlorophenyl)(3,4-dimethoxyphenyl)borinic acid was prepared from 3,4-dimethoxyphenylmagnesium bromide and 3-chlorophenylboronic acid ethylene glycol ester by the procedure described in Example 6a. The title complex product was made by the methodology described in Section 5.3.7.1, and obtained as yellow crystals. MS (ESI, positive): m/z=404 (M+1); 1H NMR (DMSO-d6, 300 MHz): δ 9.17 (d, 1H), 8.78 (d, 1H), 7.90 (dd, 1H), 7.70 (t, 1H), 7.43 (d, 1H), 7.30-7.17 (m, 5H), 6.89-6.80 (m, 3H), 3,66 (s, 3H) and 3.62 (s, 3H) ppm.

Workup

  1. customobtained as yellow crystals

Sources & evidence

ORD record
ord-44af01f9e8b24b36b3e2c4716540a207
Source dataset
uspto-grants-2008_07
Patent number
US07393856B2

Reaction notes

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