Ethylorthoformate → HCID 118093824, compound

HRID 1057008Notes

Reaction equation

HRID 1057008 reaction equation
[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([Br:15])[CH:5]=[CH:4][C:3]=1[OH:16].[CH:17]([O-])([O-])OCC>>[Br:15][C:6]1[CH:5]=[CH:4][C:3]2[O:16][CH:17]=[N:1][C:2]=2[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 53630039EthylorthoformateHCID 118093778HCID 118093778, compound

Product 1

HCID 118093824HCID 118093824, compoundYield 97%

Procedure

A solution of 2-amino-4-bromo-3-phenoxyphenol (0.075 g, 0.268 mmol) in ethyl orthoformate (0.405 mL, 2.43 mmol) was heated at 100° C. for 2.5 h. after which time the reaction mixture was cooled to RT and concentrated in vacuo to a crude residue. Purification by flash column chromatography (100% hexanes to 50% EtOAc/hexanes) gave the desired product (75.1 mg, 97%) as a white solid. LCMS calculated for C13H9BrNO2 (M+H)+: m/z=290.0, 292.0. found: 289.9, 291.9.

Workup

  1. concentrationconcentrated in vacuo to a crude residue
  2. customPurification by flash column chromatography (100% hexanes to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1df4a73505fa4dcb8b675b89c445c485
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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