Bromine → HCID 67080498, compound

HRID 1021404Notes

Reaction equation

HRID 1021404 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH2:7][CH2:6][CH:5]2[C:13]([O:15][CH2:16][CH3:17])=[O:14].[Br:18]Br>C(O)(=O)C>[Br:18][C:10]1[C:11]([OH:12])=[C:2]([Cl:1])[CH:3]=[C:4]2[C:9]=1[O:8][CH2:7][CH2:6][CH:5]2[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 53393319Ethyl-6-chloro-7-hydroxy-3,4-dihydro-2H-chromene-4-carboxylate

Product 1

HCID 67080498HCID 67080498, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of ethyl 6-chloro-7-hydroxychroman-4-carboxylate (5.14 g, 20.0 mmol) in glacial acetic acid (50 mL) at ambient temperature was added bromine (1.2 mL, 24 mmol), in six equal portions, waiting 30-60 seconds between each addition for the bromine color to be discharged. Following completion of addition, the solution was concentrated and the residue concentrated from toluene, then partitioned between ethyl acetate (200 mL) and 5% sodium bisulfite (100 mL). The organic was layer dried over sodium sulfate, then stirred with activated charcoal (2 g) at ambient temperature for 20 minutes. The charcoal was removed by filtration through a glass microfibre filter and the filtrate was concentrated to afford ethyl 8-bromo-6-chloro-7-hydroxychroman-4-carboxylate as a light brown oil (6.05 g, 90% yield).

Workup

  1. additioncompletion of addition
  2. concentrationthe solution was concentrated
  3. concentrationthe residue concentrated from toluene
  4. custompartitioned between ethyl acetate (200 mL) and 5% sodium bisulfite (100 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe charcoal was removed by filtration through a glass microfibre
  7. filtrationfilter
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4ab3945a841c4f01ae586c5bad745c4f
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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