HCID 20084379, compound → 8-Fluoro-isochroman-1,3-dione

HRID 1962405Notes

Reaction equation

HRID 1962405 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:6]=1[C:7]([OH:9])=[O:8])(O)=[O:2]>C(Cl)(=O)C>[F:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:5]2[C:6]=1[C:7](=[O:9])[O:8][C:1](=[O:2])[CH2:4]2

Participants

3

Reactant 1

HCID 20084379HCID 20084379, compound

Product 1

HCID 577334018-Fluoro-isochroman-1,3-dioneYield 102.5%

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent

Procedure

2-Carboxymethyl-6-fluoro-benzoic acid (130 mg, 0.65 mmol) in acetyl chloride (2 ml) was heated under microwave irradiation at 150° C. for 10 min then concentrated in vacuo to give the title product (120 mg, 100% yield). The compound is hydroscopic and slowly decomposes back to the starting diacid in wet solvents or under moisturised atmosphere. 1H NMR (500 MHz, DMSO-d6): 4.29 (s, 2H), 7.27 (d, J=7.8 Hz, 1H), 7.34 (dd, J=8.5 Hz, J=11 Hz, 1H), 7.76 (dt, J=5.3 Hz, J=8 Hz, 1H).

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-27b23a4ed73c48029ab2088e23146074
Source dataset
uspto-grants-2013_04
Patent number
US08415373B2

Reaction notes

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