Boron tribromide → HCID 66869566, compound

HRID 1992629Notes

Reaction equation

HRID 1992629 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16]C)[CH:14]=2)[CH:9]=[CH:8][C:7]=1[Cl:18])[CH3:2].B(Br)(Br)Br>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:16])[CH:14]=2)[CH:9]=[CH:8][C:7]=1[Cl:18])[CH3:2]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 66869528HCID 66869528, compound

Product 1

HCID 66869566HCID 66869566, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

(2-Chloro-7-methoxy-naphthalen-1-yl)-acetic acid ethyl ester (12.0 g, 43.10 mmol) and tetrabutylammonium iodide (20.7 g, 56.04 mmol) are dissolved under an atmosphere of argon in CH2Cl2 (240 ml). The reaction mixture is cooled to −78° C. and a 1 M solution of BBr3 in CH2Cl2 (108 ml, 107.77 mmol) is added during 30 minutes. After stirring at −78° C. for 15 minutes and at RT for 1 h, TLC analysis indicates complete consumption of starting material. A sat. aqueous solution of NaHCO3 (8 ml) is carefully added. The organic layer is separated, washed with brine, dried over Na2SO4 and concentrated. Purification by FCC (hexane/EtOAc 4:1 to 3:2) yields the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.51 (t, J=9.9 Hz, 3H), 4.43 (q, J=9.9 Hz, 2H), 4.48 (s, 2H), 6.28-6.36 (br, 1H), 7.29-7.32 (m, 1H), 7.48-7.49 (m, 1H), 7.58 (d, J=10 Hz, 1H), 7.89 (d, J=10 Hz, 1H), 7.96 (d, J=10 Hz, 1H). ES+−MS: 265.2, 267.2 [M+H]+.

Workup

  1. customconsumption of starting material
  2. additionA sat. aqueous solution of NaHCO3 (8 ml) is carefully added
  3. customThe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by FCC (hexane/EtOAc 4:1 to 3:2)

Sources & evidence

ORD record
ord-490fe28feacf4ac781d5e9d719f3ab27
Source dataset
uspto-grants-2010_01
Patent number
US07648989B2

Reaction notes

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