Boron tribromide → 4-{2-[5-Benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-ethyl}-benzene-1,2-diol

HRID 556117Notes

Reaction equation

[CH2:1]([C:8]1[S:12][C:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[C:17]([O:23]C)[CH:16]=2)=[N:10][C:9]=1[C:25]1[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>>[CH2:1]([C:8]1[S:12][C:11]([CH2:13][CH2:14][C:15]2[CH:16]=[C:17]([OH:23])[C:18]([OH:21])=[CH:19][CH:20]=2)=[N:10][C:9]=1[C:25]1[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 579916295-Benzyl-2-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-(4-methoxy-phenyl)-thiazole

Product 1

HCID 579915904-{2-[5-Benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-ethyl}-benzene-1,2-diolYield 52.2%

Procedure

A procedure similar to that in Example 7 was used. 5-benzyl-2-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-(4-methoxy-phenyl)-thiazole prepped in step 4 of Example 77 and boron tribromide were as starting materials, the crude product was recrystallized with acetone to obtain a product as a white solid in a yield of 52.2%, mp: 177-178 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 2.82 (2H, t, J=8.16 Hz, ArH), 3.11 (2H, t, J=8.16 Hz, ArH), 4.20 (2H, s, CH2), 6.48 (1H, d, J=8.12 Hz, ArH), 6.58˜6.64 (2H, m, ArH), 6.82 (2H, d, J=8.40 Hz, ArH), 7.14˜7.26 (3H, m, ArH), 7.32 (2H, t, J=7.28 Hz, ArH), 7.44 (2H, d, J=8.40 Hz, ArH), 8.69 (1H, s, OH), 8.75 (1H, s, OH), 9.61 (1H, s, OH); EI-MS m/e (%): 403.2 (M+, 67), 281.2 (100); HREI-MS Calcd. for C24H21NO3S: 403.1242. found: 403.1238.

Workup

customthe crude product was recrystallized with acetone

Sources & evidence

ORD record: ord-d598fc0134f643b8bf5e80f37d68fb8b
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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