Hydrochloric Acid → (6-Methoxy-1-benzothiophen-2-yl)boronic acid

HRID 993

反応式

HRID 993 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[CH:9][S:8][C:7]=2[CH:11]=1.C([Li])CCC.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.Cl>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([B:17]([OH:22])[OH:18])[S:8][C:7]=2[CH:11]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 136342376-Methoxy-1-benzothiopheneHCID 178418339Butyllithium

生成物 1

HCID 10560276(6-Methoxy-1-benzothiophen-2-yl)boronic acid収率 71%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 6-methoxybenzo[b]thiophene (18.13 g, 0.111 mol) in 150 mL of anhydrous tetrahydrofuran (THF) at -60° C. was added n-butyllithium (76.2 mL, 0.122 mol, 1.6M solution in hexanes), dropwise via syringe. After stirring for 30 minutes, triisopropyl borate (28.2 mL, 0.122 mol) was introduced via syringe. The resulting mixture was allowed to gradually warm to 0° C. and then distributed between 1N hydrochloric acid and ethyl acetate (300 mL each). The layers were separated, and the organic layer was dried over sodium sulfate. Concentration in vacuo produced a white solid that was triturated from ethyl ether hexanes. Filtration provided 16.4 g (71%) of 6-methoxybenzo[b]thiophene-2-boronic acid as a white solid. mp 200° C. (dec). 1H NMR (DMSO-d6) d 7.83 (s, 1H), 7.78 (d, J=8.6 Hz, 1H), 7.51 (d, J=2.0 Hz, 1H), 6.97 (dd, J=8.6, 2.0 Hz, 1H), 3.82 (s, 3H). FD mass spec: 208.

後処理

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationConcentration in vacuo
  4. customproduced a white solid
  5. customthat was triturated from ethyl ether hexanes
  6. filtrationFiltration

出典と根拠

ORDレコード
ord-b667ae6e1894401594ee757404717db3
出典データセット
uspto-grants-1998_03
特許番号
US05723474

関連ノート

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