Boron Trichloride → HCID 15643883, compound

HRID 2210261Notes

Reaction equation

HRID 2210261 reaction equation
B(Cl)(Cl)Cl.C[O:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=1[C:12](=[O:17])[CH:13]=[C:14]([CH3:16])[CH3:15].[K+].[Br-]>ClCCl>[OH:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=1[C:12](=[O:17])[CH:13]=[C:14]([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 25135Boron TrichlorideHCID 253877Potassium BromideHCID 156438821-(3-Methoxythiophen-2-yl)-3-methylbut-2-en-1-one

Product 1

HCID 15643883HCID 15643883, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron trichloride, (1.0 M in dichloromethane, 800 mL, 0.80 mol) was slowly added to a solution of 3-methoxy-2-(3-methyl-1-oxo-2-buten-1-yl)thiophene (52.3 g, 0.27 mol) in dichloromethane (400 mL) at -10° C. to 5° C. The resultant solution was stirred an additional 1.5 h at -5° C. Ice water was added slowly with rapid stirring. The organic layer was separated, dried over sodium sulfate, and eluted through a pad of silica gel. The solvent was evaporated in vacuo and the resultant oil was crystallized from hexanes at -70° C. to give the product, 40.0 g (82%), as a yellow solid: mp 32°-33° C.; IR (KBr): 1641, 1581 and 1541 cm-1 ; MS: m/z 183 (MH+); 1H NMR (CDCl3): δ2.00 (d, J=1.1 Hz, 3H), 2.30 (d, J=1.0 Hz, 3H), 6.25 (m, 1H), 6.75 (d, J=5.3 Hz, 1H), 7.37 (d, J=5.3 Hz, 1H) and 12.14 (s, exchanges with D2O, 1H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. washeluted through a pad of silica gel
  4. customThe solvent was evaporated in vacuo
  5. customthe resultant oil was crystallized from hexanes at -70° C.
  6. customto give the product, 40.0 g (82%)

Sources & evidence

ORD record
ord-f1b508ef950d4d39b69bcb39d66a640c
Source dataset
uspto-grants-1995_10
Patent number
US05457212

Reaction notes

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