Bromine → 2-Bromo-5-(morpholin-4-ylmethyl)phenol

HRID 1245855Notes

Reaction equation

HRID 1245855 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:15]Br>C(O)(=O)C>[Br:15][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:9][C:10]=1[OH:14]

Participants

4

Reactant 2

HCID 24408BromineHCID 132775773-(Morpholinomethyl)phenol

Product 1

HCID 219144342-Bromo-5-(morpholin-4-ylmethyl)phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-(Morpholin-4-ylmethyl)phenol (9.65 g) in glacial acetic acid (60 ml) was treated over 2 h with bromine (2.88 ml) in acetic acid (8 ml), evaporated to near dryness, water (100 ml) added and basified with 0.880 ammonia, extracted with ethyl acetate, washed with water, brine, dried (MgSO4) and evaporated to dryness to give an oil, which was purified by column chromatography eluting with 1:1 ether/isohexane to give the desired product as an oil (4.75 g).

Workup

  1. customevaporated
  2. additionadded
  3. extractionextracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness
  7. customto give an oil, which
  8. customwas purified by column chromatography
  9. washeluting with 1:1 ether/isohexane

Sources & evidence

ORD record
ord-1ffba32e408042628d2516481ad00a57
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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