Boron tribromide → HCID 135524526, compound

HRID 1816404Notes

Reaction equation

HRID 1816404 reaction equation
C[O:2][C:3]1[CH:25]=[CH:24][C:6]2[C:7]([C:10]3[CH:15]=[C:14]([CH2:16][CH2:17][CH3:18])[C:13]([O:19]C)=[CH:12][C:11]=3[CH2:21][CH2:22][CH3:23])=[N:8][O:9][C:5]=2[CH:4]=1.B(Br)(Br)Br>ClCCCl>[OH:19][C:13]1[C:14]([CH2:16][CH2:17][CH3:18])=[CH:15][C:10]([C:7]2[C:6]3[CH:24]=[CH:25][C:3]([OH:2])=[CH:4][C:5]=3[O:9][N:8]=2)=[C:11]([CH2:21][CH2:22][CH3:23])[CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22493724HCID 22493724, compound

Product 1

HCID 135524526HCID 135524526, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-methoxy-3-(4-methoxy-2,5-dipropylphenyl)-1,2-benzisoxazole (193 mg, 0.57 mmol) in 1,2-dichloroethane (6.0 mL) at 0° C. was added BBr3 (5.7 mL, 5.7 mmol, 1.0 M in CH2Cl2) slowly. The resulting brown solution was stirred at 60° C. for 15 hr, cooled to 0° C., quenched carefully with water, and extracted in EtOAc (2×30 mL) with 2 N HCl (2×20 mL). Purification (twice) by flash chromatography with silica gel (gradient to 40% EtOAc/hexanes) furnished the title compound as a light yellow solid (163 mg, 93% yield): mp 162-163° C.; 1H NMR (300 MHz, acetone-d6) δ 0.80 (t, 3H, J=7.3 Hz), 0.97 (t, 3H, J=7.4 Hz), 1.52 (m, 2H), 1.67 (m, 2H), 2.65 (two overlapping triplets, 4H), 6.91 (s, 1H), 6.95 (dd, 1H, J=8.6, 2.0 Hz), 7.04 (d, 1H, J=1.8 Hz), 7.26 (s, 1H), 7.46 (d, 1H, J=8.6 Hz), 8.89 (broad s, 2H); MS m/e 312 (M+H)+.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched carefully with water
  3. extractionextracted in EtOAc (2×30 mL) with 2 N HCl (2×20 mL)
  4. customPurification (twice) by flash chromatography with silica gel (gradient to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f7766b5e1d014dafadb9004d4e965093
Source dataset
uspto-grants-2005_04
Patent number
US06884814B2

Reaction notes

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