Boron tribromide → HCID 23296008, compound

HRID 1954283Notes

Reaction equation

HRID 1954283 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[C:8]([CH2:14][CH3:15])[CH:7]=1)=[O:5].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:14][CH3:15])[CH:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23295997HCID 23295997, compound

Product 1

HCID 23296008HCID 23296008, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At -78° C., to a stirred solution of 4-(2-chlorobenzoyl)-2-ethylanisole (18 g, 65.5 mmol) in CH2Cl2 (295 mL) was added boron tribromide (12.4 mL, 0.131 mol). After the addition was complete, the reaction was allowed to warm to ambient temperature and stirred for 48 h. The reaction was slowly poured into crushed ice (200 g) and extracted with CH2Cl2. The organic extracts were washed with sat. aq. KH2PO4 (1×) and extracted with 2.5N NaOH. The aqueous extracts were washed with CH2Cl2 (1×), acidified with 2N HCl and extracted with CH2Cl2, dried (Na2SO4) and concentrated to give 14.48 g (85%) of the title compound. 1H NMR: consistent. mass spectrum (+ESI) m/z 261 (M+H). Anal. Calcd. for C15H13ClO2.0.2H2O: C, 68.16; H, 5.11; N, 0.00. Found: C, 68.18; H, 5.15; N, 0.00.

Workup

  1. additionAfter the addition
  2. additionThe reaction was slowly poured
  3. extractionextracted with CH2Cl2
  4. washThe organic extracts were washed with sat. aq. KH2PO4 (1×)
  5. extractionextracted with 2.5N NaOH
  6. washThe aqueous extracts were washed with CH2Cl2 (1×)
  7. extractionextracted with CH2Cl2
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bc84e33f0c5b4dff9f3b19203e47e73f
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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