Boron tribromide → HCID 10168177, compound

HRID 1352237Notes

Reaction equation

HRID 1352237 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:7]=[C:8]([CH2:34][C:35]([OH:37])=[O:36])[CH:9]=[C:10]([Br:33])[C:11]=1[O:12][C:13]1[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[CH:16]=[C:15](OC)[C:14]=1[C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=1>C(Cl)Cl>[Br:33][C:10]1[CH:9]=[C:8]([CH2:34][C:35]([OH:37])=[O:36])[CH:7]=[C:6]([Br:5])[C:11]=1[O:12][C:13]1[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([O:12][CH2:13][CH2:18][C:17]([CH3:19])=[CH2:16])=[CH:15][C:14]=1[C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69513028HCID 69513028, compound

Product 1

HCID 10168177HCID 10168177, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of BBr3 in CH2Cl2 (12 mL, 12 mmol) was added slowly with a syringe to a stirred solution of 3,5-dibromo-4-[5-isopropylmethoxy-2-(3-methylbenzoyl)phenoxy]-phenylacetic acid (2 g, 3.5 mmol) in 20 mL CH2Cl2 at −20° C. After 15 min at −20° C. the solution was allowed to reach room temperature. After an additional 1 h at room temperature, the solution was poured onto ice and extracted three times with EtOAc. The combined extracts were dried over MgSO4 and concentrated to give the title compound which was used in the next step without further purification. 1H NMR (CDCl3): δ 7.8–7.7 (m, 2H), 7.5 (s, 2H), 7.4−7.3 (m, 2H), 6.9 (s, 1H), 6.2 (s, 1H), 3.6 (s, 2H), 3.3–3.2 (m, 1H), 2.4 (s, 3H), 1.1 (d, 6H).

Workup

  1. customto reach room temperature
  2. waitAfter an additional 1 h at room temperature
  3. additionthe solution was poured onto ice
  4. extractionextracted three times with EtOAc
  5. dry with materialThe combined extracts were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-262d58fed86c4a75bfc157c435836859
Source dataset
uspto-grants-2007_05
Patent number
US07220752B2

Reaction notes

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