Boron tribromide → HCID 22123618, compound

HRID 1859350Notes

Reaction equation

HRID 1859350 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][S:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][S:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22123585HCID 22123585, compound

Product 1

HCID 22123618HCID 22123618, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-(9-pentylthiononyl)thiochroman (230 mg, 0.435 mmol) in dry dichloromethane (20 ml) was added dropwise 1M solution of boron tribromide in dichloromethane (3.04 ml, 3.04 mmol) at -78° C. and stirred at the same temperature for one hour. Then the reaction mixture was warmed to room temperature and stirring was continued for additional 10 hours. The reaction mixture was quenched with water and then diluted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen sulfide solution and water, dried over magnesium sulfate, filtered and evaporated. The concentrate was subjected to flash silica gel chromatography (hexane:ethyl acetate=9:1) to obtain 178 mg (yield: 82%) of the title compound as a colorless oil.

Workup

  1. stirringstirring
  2. waitwas continued for additional 10 hours
  3. customThe reaction mixture was quenched with water
  4. additiondiluted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium hydrogen sulfide solution and water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-7da2587884bf4103b0e3f52a36b1ef9f
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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