Water → HCID 86757174, compound

HRID 1386481Notes

Reaction equation

HRID 1386481 reaction equation
P(Br)(Br)[Br:2].O[CH2:6][CH:7]1[CH2:12][C:11]([CH3:14])([CH3:13])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[S:8]1.O>C1(C)C=CC=CC=1>[Br:2][CH2:6][CH:7]1[CH2:12][C:11]([CH3:14])([CH3:13])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[S:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 86757173HCID 86757173, compound

Product 1

HCID 86757174HCID 86757174, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorus tribromide (1 ml, 10.7 mmol) is added drop by drop with a syringe at between 20 and 25° C. to a solution of the previous 6-(hydroxymethyl-4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyrane (1.85 g, 8.9 mmol) in 6.2 ml of anhydrous toluene. The mixture was left to agitate for 1 hour and then hydrolysed at 0° C. by ice and then by water. This was then extracted with ethyl ether, dried over MgSO4, filtered and the solvents evaporated. 2.14 g of 6-(bromomethyl-4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyrane is obtained (gross yield=88%).

Workup

  1. waitThe mixture was left
  2. customhydrolysed at 0° C.
  3. extractionThis was then extracted with ethyl ether
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents evaporated

Sources & evidence

ORD record
ord-28434322ef704df0afa2dcd15180acc7
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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