Bromine → HCID 23286093, compound

HRID 369370Notes

Reaction equation

HRID 369370 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[CH2:18][CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[BrH:32].BrBr>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH2:16][Br:32])=[CH:11][C:10]=1[CH2:18][CH2:19][O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 23286094HCID 23286094, compound

Product 1

HCID 23286093HCID 23286093, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4'-Benzyloxy-3'-(2-benzyloxyethyl)acetophenone (8.0 g) and 30% hydrogen bromide acetic acid solution (0.4 ml) were dissolved in chloroform (80 ml), and a solution of bromine (1.1 ml) in chloroform (30 ml) was added dropwise to the solution over 2 hours at room temperature with stirring, then the resulting mixture was concentrated in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=2/1) gave 4'-benzyloxy-3'-(2-benzyloxyethyl)-2-bromoacetophenone (3.9 g) having a melting point of 53-56° C.

Workup

  1. concentrationthe resulting mixture was concentrated in vacuo
  2. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=2/1)

Sources & evidence

ORD record
ord-de693fa786d74eeebf8def4c809cfc38
Source dataset
uspto-grants-2000_10
Patent number
US06136852

Reaction notes

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