Methanol → HCID 15526061, compound

HRID 1528179Notes

Reaction equation

HRID 1528179 reaction equation
BrB(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([N:16]([CH3:18])[CH3:17])(=[O:15])=[O:14].CO>ClCCl>[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([N:16]([CH3:18])[CH3:17])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 11183508HCID 11183508, compound

Product 1

HCID 15526061HCID 15526061, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

200 ml (200 mmol, 4.9 eq) of a 1 M solution of tribromoborane in dichloromethane were added dropwise to a solution of 8.78 g (40.8 mmol, 1 eq) of 2-methoxy-N,N-dimethylbenzenesulfonamide in 250 ml of dichloromethane at −70° C. under nitrogen. The reaction medium was left at −70° C. for one hour and was then left to return to 10° C. for one and a half hours. The reaction medium was then cooled to −70° C. and approximately 100 ml of methanol were added dropwise (approximately one hour of addition). The reaction medium was then left to return to ambient temperature and was concentrated. The residue obtained was filtered off on silica with the eluent 6/4 heptane/ethyl acetate. 7.81 g of product were obtained in the form of a beige solid. Yield=95%.

Workup

  1. waitwas then left
  2. waitto return to 10° C. for one and a half hours
  3. addition(approximately one hour of addition)
  4. waitThe reaction medium was then left
  5. customto return to ambient temperature
  6. concentrationwas concentrated
  7. customThe residue obtained
  8. filtrationwas filtered off on silica with the eluent 6/4 heptane/ethyl acetate

Sources & evidence

ORD record
ord-b22eaa84609e4031afc26603fa801989
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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