Reserpine → 4,4,5,5-Tetramethyl-2-(3-nitro-4-phenoxyphenyl)-1,3,2-dioxaborolane

HRID 51586Notes

Reaction equation

HRID 51586 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]([N+:15]([O-:17])=[O:16])[CH:3]=1.O(C1C=CC([B:33]2[O:37][C:36]([CH3:39])([CH3:38])[C:35]([CH3:41])([CH3:40])[O:34]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>[C:9]1([O:8][C:5]2[CH:6]=[CH:7][C:2]([B:33]3[O:37][C:36]([CH3:39])([CH3:38])[C:35]([CH3:41])([CH3:40])[O:34]3)=[CH:3][C:4]=2[N+:15]([O-:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 5770ReserpineHCID 161094494-Bromo-2-nitro-1-phenoxybenzeneHCID 227363402-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzonitrile

Product 1

HCID 669153784,4,5,5-Tetramethyl-2-(3-nitro-4-phenoxyphenyl)-1,3,2-dioxaborolane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared in a 56% from 4-bromo-2-nitro-1-phenoxybenzene 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 8.19(d, 1H), 7.91(d, 1H), 7.46(t, 2H), 7.27(t, 1H), 7.14(d, 2H), 7.06(d, 1H), 1.31(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 14.02 min.

Workup

  1. customtr 14.02 min.

Sources & evidence

ORD record
ord-f03eee2555c84e3d88d2ab1967ae23fe
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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