Bromine → HCID 20069058, compound

HRID 982103Notes

Reaction equation

HRID 982103 reaction equation
[Br:1][CH2:2][CH:3]1[C:8]2[C:9]([CH3:15])=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:7]=2[CH2:6][CH:5]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[O:4]1.[Br:22]Br.S(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:22][C:11]1[CH:10]=[C:9]([CH3:15])[C:8]2[CH:3]([CH2:2][Br:1])[O:4][CH:5]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:6][C:7]=2[C:12]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 24408BromineHCID 20069120HCID 20069120, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 20069058HCID 20069058, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.04 g (5.8 mmol) of 1-bromomethyl-3-cyclohexyl-3,4-dihydro-5-methoxy-8-methyl-1H-2-benxopyran (the product of Step 2 of Example 33) in 20 mL of dry methylene chloride was cooled to 0° C. and treated with 0.38 mL (7.4 mmol) of bromine. The resultant solution was stirred for 25 minutes at 0° C. and then poured into 30 mL of a saturated aqueous solution of sodium bisulfite. The cloudy mixture was extracted with 200 mL of diethyl ether and the organic extract was washed with saturated aqueous sodium bicarbonate solution, water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was crystallized from hexane/ether to afford 1.36 g (55% yield) of the title compound.

Workup

  1. extractionThe cloudy mixture was extracted with 200 mL of diethyl ether
  2. extractionthe organic extract
  3. washwas washed with saturated aqueous sodium bicarbonate solution, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from hexane/ether

Sources & evidence

ORD record
ord-0fbc109e6fc1406fab370bc485d346de
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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