Reserpine → 2-(3-Chloro-4-phenoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 51576

Reaction equation

HRID 51576 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([Cl:15])[CH:3]=1.O(C1C=CC([B:31]2[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:39])([CH3:38])[O:32]2)=CC=1C#N)C1C=CC=CC=1.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[Cl:15][C:4]1[CH:3]=[C:2]([B:31]2[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:39])([CH3:38])[O:32]2)[CH:7]=[CH:6][C:5]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 5770ReserpineHCID 227363094-Bromo-2-chloro-1-phenoxybenzeneHCID 227363402-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzonitrile

Product 1

HCID 227362172-(3-Chloro-4-phenoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (472 mg, 81%) was prepared from 4-bromo-2-chloro-1-phenoxybenzene (500 mg, 1.77 mmol) in a similar manner to that described for the preparation 2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzonitrile: 1H NMR (DMSO-d6, 400 MHz) δ 7.75(s, 1H), 7.60 (d, 1H), 7.42(t, 2H), 7.21(t, 1H), 7.02 (m, 3H), 1.30(s, 12H); RP-HPLC (Hypersil HS, 5 μm, 100 A 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 15.53 min.

Workup

  1. customtr 15.53 min.

Sources & evidence

ORD record
ord-ff11ae08660144859675c170f1c5e7a9
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Linked notes

Loading…