Bromine → HCID 87464204, compound

HRID 877284Notes

Reaction equation

HRID 877284 reaction equation
[Br:1]Br.[CH:3]([C:5]1([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH3:21])[CH:10]=[CH:9][CH:8]=[CH:7][CH2:6]1)=[O:4].S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH:3]([C:5]1([C:11]2[CH:20]=[C:19]([Br:1])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH3:21])[CH:6]=[CH:7][CH:8]=[CH:9][CH2:10]1)=[O:4]

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 86643579HCID 86643579, compound

Product 1

HCID 87464204HCID 87464204, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 19.5 ml (380 mmol) of bromine and 300 ml of dichloromethane is added dropwise with exclusion of light to a solution, cooled to 0° C., of 86.2 g (350 mmol) of 2-(1-formylphenyl)-1-naphthylmethane in 1500 ml of dichloromethane. After stirring for a further 3 h, 1000 ml of 5% sodium sulfite solution are added, the mixture is stirred briefly, the organic phase is separated off, washed three times with 500 ml of water and evaporated in vacuo, and the residue is taken up in a little acetone. After standing for 24 h, the crystals are filtered off with suction, washed with acetone:n-hexane (1:1) and dried in vacuo. Yield: 90.7 g (279 mmol), 79.7%, purity about 98% (NMR).

Workup

  1. additionis added dropwise with exclusion of light to a solution
  2. stirringthe mixture is stirred briefly
  3. customthe organic phase is separated off
  4. washwashed three times with 500 ml of water
  5. customevaporated in vacuo
  6. waitAfter standing for 24 h
  7. filtrationthe crystals are filtered off with suction
  8. washwashed with acetone:n-hexane (1:1)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a1c60fc9527f4a52aaf2501cb0ad0b12
Source dataset
uspto-grants-2015_03
Patent number
US08986852B2

Reaction notes

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