Tetrahydrofuran → 32273-01-1

HRID 1253932Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[C:5]([F:9])=[CH:4][C:3]=1[OH:10].C1C[O:14][CH2:13]C1.C1N=CN(C(N2C=NC=C2)=O)C=1>CCOC(C)=O>[Br:8][C:6]1[C:5]([F:9])=[CH:4][C:3]2[O:10][C:13](=[O:14])[NH:1][C:2]=2[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A flask was charged with 2-amino-4-bromo-5-fluorophenol (3.3 g, 18.84 mmol) and THF (200 mL), and CDI (3.05 g, 18.84 mmol) was added. The mixture was heated to 60° C. for 2 h. The mixture was diluted with EtOAc and washed with 1N HCl in water. The organic phase was dried over Na2SO4 and concentrated to give 5-bromo-6-fluorobenzo[d]oxazol-2(3H)-one. 1H NMR (400 MHz, DMSO-d6) δppm 7.38 (d, J=6.06 Hz, 1H) 7.56 (d, J=8.34 Hz, 1H) 11.88 (br. s., 1H).

Workup

additionwas added
washwashed with 1N HCl in water
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-1251aa78d06d4940bf0e8acb0023e070
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455522B2

Reaction notes

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