1-Bromo-3,5-difluorobenzene → 6-(3,5-Difluoro-phenyl)-4,4dimethyl-1,4dihydrobenzo-[d][1,3]oxazin-2-one

HRID 2099206Notes

Reaction equation

HRID 2099206 reaction equation
[CH3:1][C:2]1([CH3:16])[C:7]2[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:15])[O:3]1.Br[C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=1>>[F:24][C:22]1[CH:23]=[C:18]([C:9]2[CH:10]=[CH:11][C:6]3[NH:5][C:4](=[O:15])[O:3][C:2]([CH3:16])([CH3:1])[C:7]=3[CH:8]=2)[CH:19]=[C:20]([F:25])[CH:21]=1

Participants

3

Reactant 2

HCID 1363131-Bromo-3,5-difluorobenzeneHCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid

Product 1

HCID 98356156-(3,5-Difluoro-phenyl)-4,4dimethyl-1,4dihydrobenzo-[d][1,3]oxazin-2-one

Procedure

6-(3,5-difluoro-phenyl)-4,4-dimethyl-1,4-dihydrobenzo-[d][1,3]oxazin-2-one was prepared, according to the procedure of Example 5 from (4,4-dimethyl-1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 1-bromo-3,5-difluorobenzene, as a white solid: mp 218-219° C.; 1H-NMR (DMSO-d6) δ 10.4 (s, 1H), 7.67-7.65 (m, 2H), 7.49 (d, 2H, J=7.73 Hz), 7.19 (t, 1H, J=9.29 Hz), 6.96 (d, 1H, J=8.88 Hz), 1.7 (s, 6H); MS (APCI) m/z 290 ([M+H]+, 100%); Anal. Calcd. For C16H13F2NO2: C, 66.43; H, 4.53; N, 4.84. Found: C, 66.01; H, 4.46; N, 4.67.

Sources & evidence

ORD record
ord-6c7a0627befe41f88b352c68962638c1
Source dataset
uspto-grants-2009_08
Patent number
US07569564B2

Reaction notes

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