Toluene → 6-Bromo-2,4,4-trimethyl-2,4-dihydro-1H-benzo[D][1,3]oxazine

HRID 277847Notes

Reaction equation

HRID 277847 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([OH:12])([CH3:11])[CH3:10].[C:13]1(C)C=CC=C[CH:14]=1>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][CH:13]([CH3:14])[O:12][C:9]([CH3:10])([CH3:11])[C:3]=2[CH:4]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 120422752-(2-Amino-5-bromophenyl)propan-2-ol

Product 1

HCID 234355746-Bromo-2,4,4-trimethyl-2,4-dihydro-1H-benzo[D][1,3]oxazineYield 78%

Procedure

To a solution of 2-(2-amino-5-bromophenyl)propan-2-ol (27 g, 125 mmol) in anhydrous toluene was added at ambient temperature under a blanket of nitrogen acetylaldehyde (10.5 mL, 187 mmol). After 10 minutes, the mixture was passed through a pad of silica gel and filtrate was concentrated to yield 6-bromo-2,4,4-trimethyl-1,4-dihydro-2H-3,1-benzoxazine as off-white solid (25 g, 78%): 1H-NMR (DMSO-d6) δ 7.22 (d, 1H, J=2.2 Hz), 7.08 (dd, 1H, J=8.6, 2.3 Hz), 6.51 (d, 1H, J=8.6 Hz), 6.36 (s, 1H), 4.72 (m, 1H), 1.45 (s, 3H), 1.40 (s, 3H), 1.25 (d, 3H, J=5.5 Hz).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-fe0277635afa4460931e7077aa53d80d
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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