1-Bromo-3-fluorobenzene → 6-(3-fluorophenyl)-4,4-dimethyl-1H-3,1-benzoxazin-2-one

HRID 2304517Notes

Reaction equation

Br[C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=[O:12])[O:8][C:9]([CH3:11])([CH3:10])[C:4]=2[CH:3]=1.Br[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1>>[F:22][C:18]1[CH:17]=[C:16]([C:2]2[CH:14]=[CH:13][C:5]3[NH:6][C:7](=[O:12])[O:8][C:9]([CH3:11])([CH3:10])[C:4]=3[CH:3]=2)[CH:21]=[CH:20][CH:19]=1

Participants

Reactant 2

HCID 140821-Bromo-3-fluorobenzene

HCID 30630Brofoxine

Product 1

HCID 97954516-(3-fluorophenyl)-4,4-dimethyl-1H-3,1-benzoxazin-2-one

Procedure

6-(3-Fluoro-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one was prepared, from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and 1-bromo-3-fluorobenzene according to the procedure of Example 4, as a light yellow solid: mp 181-182° C.; 1H-NMR (DMSO-d6) δ10.4 (s, 1H), 7.62-7.44 (m, 5H), 7.16 (t, 1H, J=2.22 Hz), 6.97 (d, 1H, J=8.83), 1.67 (s, 6H); MS (EI) m/z 271 ([M+H]+, 40%); Anal. Calc. For C16H14FNO2: C, 69.91; H, 5.3; N, 5.1. Found: C, 70.0; H, 5.32; N, 4.92.

Sources & evidence

ORD record: ord-13e5ede77f344977a840b6cf6cfe7d73
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436929B1

Reaction notes

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