Boron tribromide → HCID 69971360, compound

HRID 2298230Notes

Reaction equation

HRID 2298230 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([O:22]C)=[CH:15][C:14]=2[C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:7]([Br:32])[CH:6]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:22])=[CH:15][C:14]=2[C:24](=[O:31])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[C:7]([Br:32])[CH:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9916184HCID 9916184, compound

Product 1

HCID 69971360HCID 69971360, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-(2-Benzoyl-5-isopropyl-4-methoxy-phenoxy)-3,5-dibromo-phenyl)-acetic acid methyl ester (100 mg, 0.17 mmol) in 5 ml CH2Cl2 was cooled to −20° C. BBr3 (0.52 ml, 3 eq) was added dropwise and the reaction was allowed to reach room temperature and then poured into ice. The two phases were separated and the water phase extracted with CH2Cl2. The combined organic phases were dried over MgSO4 and concentrated. Purification on silica gel gave 69mg (71%) (4-(2-Benzoyl-5-isopropyl-4-hydroxy-phenoxy)-3,5-dibromo-phenyl)-acetic acid methyl ester as a white solid. 1H NMR (CD3COCD3): d 8.46 (s, 1H), 7.95 (d, 2H), 7.64 (s, 2H), 7.54 (m, 3H), 7.01 (s, 1H), 6.29 (s, 1H), 3.73 (s, 2H), 3.65 (s, 3H), 3.27 (m, 1H), 1.09 (d, 6H).

Workup

  1. customto reach room temperature
  2. additionpoured into ice
  3. customThe two phases were separated
  4. extractionthe water phase extracted with CH2Cl2
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated
  7. customPurification on silica gel

Sources & evidence

ORD record
ord-2f80845c491443a5a2af73fe33dc122b
Source dataset
uspto-grants-2002_12
Patent number
US06492424B1

Reaction notes

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