HCID 178498458, compound → Methyl 7-fluoro-2,3-dihydro-1,4-benzodioxine-5-carboxylate

HRID 253296Notes

Reaction equation

HRID 253296 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[CH:8]=[C:7](N=[N-])[CH:6]=1)=[O:4].[F:17][B+]F>ClC1C=CC(Cl)=CC=1Cl>[F:17][C:7]1[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[CH:8]=1

Participants

3

Reactant 1

HCID 178498458HCID 178498458, compound

Product 1

HCID 49780160Methyl 7-fluoro-2,3-dihydro-1,4-benzodioxine-5-carboxylateYield 54.5%

Reagents, catalysts & solvents 1

HCID 131,2,4-TrichlorobenzeneSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of difluoroboranylium {8-[(methyloxy)carbonyl]-2,3-dihydro-1,4-benzodioxin-6-yl}diazenide (1.0 g, 3.46 mmol) in 1,2,4-trichlorobenzene (10 mL) was heated to 110° C. and allowed to stir for 3 h. The reaction mixture was then cooled to room temperature and purified immediately by flash column chromatography (SiO2, 100% hexanes, 30% ethyl acetate/hexanes) to yield 400 mg (54%) of methyl 7-fluoro-2,3-dihydro-1,4-benzodioxine-5-carboxylate as a white powder: 1H NMR (400 MHz, CDCl3): 7.11 (dd, J=3.2, 8.8 Hz, 1H), 6.78 (dd, J=3.2, 8.8 Hz, 1H), 4.35-4.28 (m, 4H), 3.89 (s, 3H).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. custompurified immediately by flash column chromatography (SiO2, 100% hexanes, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-87aa7f7c06594c32a71dabccdffa73df
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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