Carbon tetrabromide → 4-(Bromomethyl)-2,6-dimethylphenyl acetate

HRID 43290ノート

反応式

HRID 43290 の反応式
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH2:12]O)=[CH:7][C:6]=1[CH3:14])(=[O:3])[CH3:2].[Br:15]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH2:12][Br:15])=[CH:7][C:6]=1[CH3:14])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 280655654-(Hydroxymethyl)-2,6-dimethylphenyl acetate

生成物 1

HCID 132969354-(Bromomethyl)-2,6-dimethylphenyl acetate収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of commercially available 4-(hydroxymethyl)-2,6-dimethylphenyl acetate (1 g, 5.15 mmol) and perbromomethane (2.39 g, 7.21 mmol) in tetrahydrofuran (25 mL) was added triphenylphosphine (1.620 g, 6.18 mmol). The mixture was stirred at room temperature for 6 hours then concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, hexane:ethyl acetate 4:1) to provide the title compound (1.05 g, 80% yield). MS (DCI/NH3) m/z 274 (M+NH4)+.

後処理

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (silica gel, hexane:ethyl acetate 4:1)

出典と根拠

ORDレコード
ord-316f60850f8944f7a843c8241538bade
出典データセット
uspto-grants-2013_09
特許番号
US08536336B2

反応ノート

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