Acetic Acid → 2,3,4,5-Tetrahydro-1,4-benzoxazepin-9-ol hydrobromide

HRID 1514241Notes

Reaction equation

HRID 1514241 reaction equation
C[O:2][C:3]1[C:13]2[O:12][CH2:11][CH2:10][NH:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C(O)(=O)C.C(OCC)C.[BrH:23]>>[BrH:23].[O:12]1[C:13]2[C:3]([OH:2])=[CH:4][CH:5]=[CH:6][C:7]=2[CH2:8][NH:9][CH2:10][CH2:11]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 532128959-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine

Product 1

HCID 684690182,3,4,5-Tetrahydro-1,4-benzoxazepin-9-ol hydrobromide

Conditions

Temperature
80 °C

Procedure

A suspension of 9-(methyloxy)-2,3,4,5-tetrahydro-1,4-benzoxazepine (Preparation 84) (43.4 g, 242 mmol) in 33% HBr in acetic acid (300 ml, 1823 mmol) was heated at 80° C. overnight. The mixture was allowed to cool to room temperature then treated with diethyl ether (300 ml) and stirred for 30 minutes. The resulting solid was collected by filtration, washed with diethyl ether (300 ml) and dried under vacuum at 40° C. to give the title compound as a pale brown powder (55.1 g)

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with diethyl ether (300 ml)
  4. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-476d3dbf87374b3c9e4bcdf5ebc98bdb
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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