Formaldehyde → HCID 86718777, compound

HRID 1854214Notes

Reaction equation

HRID 1854214 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1O.[CH2:9]=[O:10].[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12].[CH:16](O)(C)C>>[Br:1][C:2]1[C:7]2[O:10][CH2:9][N:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:16][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 3776IsopropanolHCID 6385Tert-ButylamineHCID 72442-Bromophenol

Product 1

HCID 86718777HCID 86718777, compound

Conditions

Temperature
68.5 °C

Procedure

To a mixture of 2-bromophenol (10.0 g, 57.8 mmol, 1.0 equiv), paraformaldehyde (8.67 g, 5 equiv) in isopropanol (80 mL) was added tert-butylamine (21.1 g, 5 equiv) dropwise. The resulting reaction mixture was stirred at 67-70° C. under nitrogen for 1.5 hours. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure to give a yellow oil. The yellow oil was purified by column chromatography to give 8-bromo-3-(tert-butyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine (9 g) as yellow oil.

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customto give a yellow oil
  5. customThe yellow oil was purified by column chromatography

Sources & evidence

ORD record
ord-8ec0fe9a11e940e3855d695272486e93
Source dataset
uspto-grants-2015_02
Patent number
US08962657B2

Reaction notes

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