(3-Chlorophenyl)boronic acid → 6-(3-Chlorophenyl)-2,4,4-trimethyl-1,4-dihydro-2H-3,1-benzoxazine

HRID 277863Notes

Reaction equation

HRID 277863 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[CH:13]=[CH:14][C:15]2[NH:20][CH:19]([CH3:21])[O:18][C:17]([CH3:23])([CH3:22])[C:16]=2[CH:24]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH:19]([CH3:21])[O:18][C:17]([CH3:23])([CH3:22])[C:16]=3[CH:24]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 234355746-Bromo-2,4,4-trimethyl-2,4-dihydro-1H-benzo[D][1,3]oxazine

Product 1

HCID 234356116-(3-Chlorophenyl)-2,4,4-trimethyl-1,4-dihydro-2H-3,1-benzoxazine

Procedure

Prepared according to the coupling procedure for Example 17 from 3-chlorophenyl boronic acid and 6-bromo-2,4,4-trimethyl-1,4-dihydro-2H-3,1-benzoxazine. A orange solid: mp 144-146° C.; 1H-NMR (CDCl3) δ 7.50 (t, 1H, J=1.78 Hz), 7.40 (dt, 1H, J=7.61, 1.45 Hz), 7.33 (t, 1H, J=7.76 Hz), 7.29-7.22 (m, 4H) 6.72 (d, 1H, J=8.24 Hz), 4.90 (q, 1H, J=5.45 Hz), 1.62 (s, 3H), 1.59 (s, 3H), 1.4 6 (d, 3H, J=5.5 Hz); MS (ES) m/z 288/290 ([M+H]+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4649a84863844ce0ae4e5e8f19e6a206
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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