Boron tribromide → HCID 69990480, compound

HRID 1417937Notes

Reaction equation

HRID 1417937 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([NH:21][C:22](=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([NH:21][C:22](=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69989407HCID 69989407, compound

Product 1

HCID 69990480HCID 69990480, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution comprising about 1.3 g of compound 9a (m=6) in 50 ml of CH2Cl2 was added 7.0 ml of boron tribromide (BBr3, 1M solution in CH2Cl2) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 2.5 h and quenched by adding about 30 ml of 1N HCl. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×30 ml). The combined organic layer was dried with Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether: EtOAc, 1:1) affording the phenol 10a (1.1 g, 88%).

Workup

  1. customquenched
  2. additionby adding about 30 ml of 1N HCl
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×30 ml)
  5. dry with materialThe combined organic layer was dried with Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (petroleum ether: EtOAc, 1:1)

Sources & evidence

ORD record
ord-0380ac66897a404cabf48fcb864f70bf
Source dataset
uspto-grants-1999_03
Patent number
US05880115

Reaction notes

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