Nitric Acid → 3-Chloro-4-nitrophenol

HRID 510456Notes

Reaction equation

HRID 510456 reaction equation
C(OC(N1C2C(=CC(OC)=CC=2Cl)C=C1B(O)O)=O)(C)(C)C.[Cl:23][C:24]1[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1.[N+:31]([O-])([OH:33])=[O:32]>C(O)(=O)C>[N+:31]([C:29]1[CH:28]=[CH:27][C:26]([OH:30])=[CH:25][C:24]=1[Cl:23])([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 79333-ChlorophenolHCID 583469401-(tert-Butoxycarbonyl)-7-chloro-5-methoxy-1H-indol-2-ylboronic acid

Product 1

HCID 102833-Chloro-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Synthesis of 1-(tert-butoxycarbonyl)-7 chloro-5 methoxy-1H-indol-2-yl boronic acid is shown in Scheme 4. Meta-chlorophenol is nitrated with fuming nitric acid in acetic acid to yield 4-nitro-3-chlorophenol, compound 4-2. The phenol is methylated with dimethylsulfate and potassium carbonate in ethanol, producing compound 4-3, which is treated with vinyl Grignard reagent and cyclized to form the indole, compound 4-4. Compound 4-4 is protected with Boc and then treated with lithium diispropylamide and triisopropylborate to produce the protected substituted boronic acid 4-6.

Sources & evidence

ORD record
ord-a6ab6bcaab3d4b90bef2f075ef864316
Source dataset
uspto-grants-2015_08
Patent number
US09096611B2

Reaction notes

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