Boron tribromide → HCID 68703464, compound

HRID 639201Notes

Reaction equation

HRID 639201 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16]C)=[CH:13][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][C:12]([OH:16])=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Cl:18])[CH3:2]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 68705206HCID 68705206, compound

Product 1

HCID 68703464HCID 68703464, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

(2-Chloro-6-methoxy-naphthalen-1-yl)acetic acid ethyl ester (5.43 g, 19.48 mmol) and tetrabutylammonium iodide (9.35 g, 25.32 mmol) are dissolved under an atmosphere of argon in CH2Cl2 (110 ml). The reaction mixture is cooled to −78° C. and a 1 M solution of BBr3 in CH2Cl2 (48.7 ml, 48.7 mmol) is added during 15 minutes. After stirring at −78° C. for 10 minutes and at RT for 10 minutes, TLC analysis indicates complete consumption of starting material. The reaction mixture is poured on conc. aqueous NaHCO3 solution, and the mixture is vigorously stirred for 20 minutes at RT. After extraction with CH2Cl2, the organic layer is washed with brine and dried over Na2SO4. Purification by FCC (hexane/EtOAc 2:1) yields the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.19 (t, J=9 Hz, 3H), 4.12 (q, J=9 Hz, 2H), 4.18 (s, 2H), 5.35-5.60 (br, 1H), 6.93 (s, 1H), 6.99 (d, J=10 Hz, 1H), 7.33 (d, J=10 Hz, 1H), 7.42 (d, J=10 Hz, 1H), 7.70 (d, J=10 Hz, 1H). ES+-MS: 265.2, 266.8 [M+H]+.

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture is poured on conc. aqueous NaHCO3 solution
  3. stirringthe mixture is vigorously stirred for 20 minutes at RT
  4. extractionAfter extraction with CH2Cl2
  5. washthe organic layer is washed with brine
  6. dry with materialdried over Na2SO4
  7. customPurification by FCC (hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-e47004c597ed448e9e615986de049458
Source dataset
uspto-grants-2010_04
Patent number
US07691861B2

Reaction notes

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