Water → 2-Cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol

HRID 1954265Notes

Reaction equation

HRID 1954265 reaction equation
[CH2:1]([C:8]1[S:9][C:10]([CH3:29])=[C:11]([CH3:28])[C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[C:17]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:16]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[CH:23]1([C:17]2[CH:16]=[C:15]([C:13]3[C:12]4[C:11]([CH3:28])=[C:10]([CH3:29])[S:9][C:8]=4[CH:1]=[C:2]4[C:7]=3[CH:6]=[CH:5][CH:4]=[CH:3]4)[CH:20]=[CH:19][C:18]=2[OH:21])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 23445655HCID 23445655, compound

Product 1

HCID 184307052-Cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenolYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (2-benzyl4,5-dimethyl-thiophen-3-yl)-(3-cyclopentyl-4-methoxy-phenyl)-methanone (4.8 g, 11.7 mmol) in anhydrous methylene chloride (70 mL) at -78° C. under nitrogen was added dropwise over a period of 20 min boron tribromide (3.6 mL, 37.6 mmol). The reaction mixture was then allowed to stir at room temperature for 22 h. The solution was poured onto a mixture of ice and water (600 mL) and extracted with diethyl ether (800 mL). The diethyl ether layer was washed twice with water (500 mL) and once with brine (500 mL). Concentration under reduced pressure and chromatography with petroleum ether:ethyl acetate (97:3) gave the title compound as a white solid (3.4 g, 78%): mp 156-158° C.; (DMSO-d6) δ 9.48 (s, 1 H), 8.42 (s, 1 H), 7.93 (d, 1 H), 7.46-7.41 (m, 2 H), 7.35-7.30 (m, 1 H), 7.00 (s, 1 H), 6.95-6.90 (m, 2 H), 3.38-3.28 (m, 1 H), 2.39 (s, 3 H), 1.99-1.90 (m, 2 H), 1.68-1.47 (m, 6 H), 1.60 (s, 3 H). MS(EI): [M+] 372. Anal. Calc. for C25H24OS: C, 80.60, H, 6.49, N, 0.00. Found: C, 80.39, H, 6.43, N, 0.04.

Workup

  1. extractionextracted with diethyl ether (800 mL)
  2. washThe diethyl ether layer was washed twice with water (500 mL) and once with brine (500 mL)
  3. concentrationConcentration under reduced pressure and chromatography with petroleum ether:ethyl acetate (97:3)

Sources & evidence

ORD record
ord-fd2137a5201d4af6b148667d01ce1011
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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