N-bromobutanimide → 7-Bromo-2,3,4,5-tetrahydro-1-benzoxepin-5-ol

HRID 1613614Notes

Reaction equation

HRID 1613614 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[CH2:4][CH2:3][CH2:2]1.[Br:13]N1C(=O)CCC1=O>C(O)(=O)C>[Br:13][C:10]1[CH:9]=[CH:8][C:7]2[O:1][CH2:2][CH2:3][CH2:4][CH:5]([OH:12])[C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3155752,3,4,5-Tetrahydro-1-benzoxepin-5-one

Product 1

HCID 197742237-Bromo-2,3,4,5-tetrahydro-1-benzoxepin-5-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

104.9 g (0.64 mole) of 2,3-dihydro-1-benzoxepin-5(4H)-one are dissolved at room temperature in 780 ml of glacial acetic acid and then, while stirring vigorously at 10° C., 113.9 g (0.64 mole) of N-bromosuccinimide are introduced in portions so that the temperature does not exceed 18°-20° C. (about 30 min). The reaction is complete after about 4 hours (TLC check) and the mixture is poured into 3 l of vigorously stirred ice-water and then stirred for 30 minutes. The solid produced which is initially oily crystallizes completely after some time. The solid is filtered off with suction and washed with about 5 l of water. It is dried over calcium chloride in vacuo and crystallized in cyclohexane.

Workup

  1. customdoes not exceed 18°-20° C.
  2. custom(about 30 min)
  3. stirringstirred for 30 minutes
  4. customThe solid produced which
  5. customis initially oily crystallizes completely after some time
  6. filtrationThe solid is filtered off with suction
  7. washwashed with about 5 l of water
  8. dry with materialIt is dried over calcium chloride in vacuo
  9. customcrystallized in cyclohexane

Sources & evidence

ORD record
ord-fc3fcd44600149e0add0f26fed766802
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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