Bromine → 2-Bromo-7-iodo-9,10-dihydrophenanthrene

HRID 511058Notes

Reaction equation

HRID 511058 reaction equation
[I:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[Br:16]Br.S([O-])(O)=O.[Na+]>P(OC)(OC)(OC)=O>[Br:16][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[C:4](=[CH:3][C:2]([I:1])=[CH:15][CH:14]=3)[CH2:5][CH2:6][C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 23665763Sodium BisulfiteHCID 576345402-Iodo-9,10-dihydrophenanthrene

Product 1

HCID 667982202-Bromo-7-iodo-9,10-dihydrophenanthrene

Reagents, catalysts & solvents 1

HCID 10541Trimethyl PhosphateSolvent2×

Procedure

9.5 g (27.9 mmol) of 2-iodo-9,10-dihydrophenanthrene are dissolved in 40 ml of trimethyl phosphate, and a solution of 2 ml (39 mmol) of bromine in 10 ml of trimethyl phosphate is added dropwise at 20° C. After 90 min, the batch is added to ice-water, excess bromine is reduced by addition of sodium hydrogensulfite soln., and the precipitated product is filtered off with suction, taken up in toluene, washed with sat. sodium hydrogen-carbonate soln. and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is recrystallised from heptane/toluene, giving 2-bromo-7-iodo-9,10-dihydrophenanthrene as colourless crystals.

Workup

  1. filtration, and the precipitated product is filtered off with suction
  2. washwashed with sat. sodium hydrogen-carbonate soln
  3. dry with materialand dried over sodium sulfate
  4. customThe solvent is removed in vacuo
  5. customthe residue is recrystallised from heptane/toluene

Sources & evidence

ORD record
ord-308024e648f344c9a2b0b9ca92d65088
Source dataset
uspto-grants-2015_08
Patent number
US09096795B2

Reaction notes

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