Boron tribromide → HCID 21996975, compound

HRID 1978234Notes

Reaction equation

HRID 1978234 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:17]C)=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:8].B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21996993HCID 21996993, compound2×

Product 1

HCID 21996975HCID 21996975, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 190 mg (0.6 mmol) of 5-bromo-2-methoxy-4′-methylbenzophenone (Compound H) in 15 mL of dichloromethane was added 0.9 mL (0.9 mmol) of boron tribromide (1M in dichloromethane) at ambient temperature. The orange solution was stirred at ambient temperature for 3 hours under a blanket of argon. The reaction mixture was cooled to −78° C., quenched with methanol and then extracted between ethyl acetate and sat. NaHCO3 (aq.) solution. The layers were separated and the organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow solid. Purification by flash chromatography (silica, 5% ethyl acetate in hexane) gave the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to −78° C.
  2. customquenched with methanol
  3. extractionextracted between ethyl acetate and sat. NaHCO3 (aq.) solution
  4. customThe layers were separated
  5. dry with materialthe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a pale yellow solid
  9. customPurification by flash chromatography (silica, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-769ce1b7b0794519a2239528ae210f53
Source dataset
uspto-grants-2001_05
Patent number
US06235923B1

Reaction notes

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