Boron tribromide → HCID 66645648, compound

HRID 1184506Notes

Reaction equation

HRID 1184506 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:18]=[CH:17][C:10]2[O:11][CH:12]([CH3:16])[C:13](=[O:15])[NH:14][C:9]=2[CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[CH:18]=[CH:17][C:10]2[O:11][CH:12]([CH3:16])[C:13](=[O:15])[NH:14][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 12213038HCID 12213038, compound

Product 1

HCID 66645648HCID 66645648, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Under N2, a 50 mL round-bottomed flask was charged with a 1M solution of BBr3 (3.11 mL, 3.11 mmol), then cooled in an ice/brine bath. To the cooled solution, was added drop-wise, 6-methoxy-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one 394B (0.2 g, 1.035 mmol) in anhydrous DCM (4 mL). The reaction was stirred under N2 and then allowed to slowly warm to 23° C. After 2 hr, ice cold water (25 mL) was slowly added to the reaction mixture. The product was collected by vacuum filtration, washed with water, and dried in vacuo to give a light tan solid (0.116 g, 62.5% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37 (d, J=6.57 Hz, 3H) 4.44-4.57 (m, 1H) 6.24-6.32 (m, 1H) 6.36 (d, J=2.78 Hz, 1H) 6.74 (d, J=8.59 Hz, 1H) 9.15 (s, 1H) 10.50 (s, 1 H). ESI-MS: m/z 180.1 (M+H)+.

Workup

  1. temperaturecooled in an ice/brine bath
  2. filtrationThe product was collected by vacuum filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d9fd922779154a4e81be61064db08612
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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