Boron Trichloride → HCID 18923992, compound

HRID 1290410Notes

Reaction equation

HRID 1290410 reaction equation
[Br:1][CH:2]1[CH2:6][S:5](=[O:8])(=[O:7])[CH:4]([CH2:9][O:10]CC2C=CC=CC=2)[CH2:3]1.B(Cl)(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[S:5](=[O:8])(=[O:7])[CH:6]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 18924006HCID 18924006, compound

Product 1

HCID 18923992HCID 18923992, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a -78° C. solution, under argon, of 4.23 g of product from Example 175 in 28 ml of dry methylene chloride is added, dropwise, 17.2 ml of 1M boron trichloride. The reaction mixture is warmed to 0° C. and stirred for 1 hour. The reaction is quenched with methyl alcohol, concentrated in vacuo and chromatographed (silica gel: 0-30% ethyl acetate/hexane) to give 2.57 g of the desired product (1:1 mixture of isomers).

Workup

  1. customThe reaction is quenched with methyl alcohol
  2. concentrationconcentrated in vacuo
  3. customchromatographed (silica gel: 0-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c200c6697867450497f151148a8a8de9
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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