Bromine → HCID 13588714, compound

HRID 1721956Notes

Reaction equation

HRID 1721956 reaction equation
[Br:1]Br.[C:3]([O:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][C:14]=1[OH:15])(=[O:5])[CH3:4]>C(Cl)(Cl)Cl.Br.C(O)(=O)C>[C:3]([O:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:16](=[O:18])[CH2:17][Br:1])[CH:12]=[CH:13][C:14]=1[OH:15])(=[O:5])[CH3:4]

Participants

6

Reactant 2

HCID 24408BromineHCID 20029755HCID 20029755, compound

Product 1

HCID 13588714HCID 13588714, compound

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideCatalystHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of bromine (0.8 ml, 2.5g) in chloroform (20 ml) was added over 20 min to a stirred solution of 1-[3-[2-(acetyloxy)ethyl]-4-hydroxyphenyl]ethanone (3.26 g ) in chloroform (50 ml) containing a few drops of 45% hydrogen bromide in acetic acid. The red solution was diluted with ER (200 ml) washed with water (100 ml), 8% sodium bicarbonate (100 ml), brine (100 ml), dried and evaporated to give the title compound as an oil which solidified on standing to give a pale pink solid (4.1 g) m.p. 89°-92°. Two recrystallisations from chloroform gave a sample with m.p. 98°-99°.

Workup

  1. additionThe red solution was diluted with ER (200 ml)
  2. washwashed with water (100 ml), 8% sodium bicarbonate (100 ml), brine (100 ml)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-1a7a297a40a64395be01d9a93f2d376a
Source dataset
uspto-grants-1989_08
Patent number
US04853381

Reaction notes

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