Carbon tetrabromide → HCID 178444389、化合物

HRID 247524ノート

反応式

HRID 247524 の反応式
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12]O)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:33]C(Br)(Br)Br>C(Cl)Cl>[Br:33][CH2:12][C@H:9]1[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]1

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178444539HCID 178444539、化合物

生成物 1

HCID 178444389HCID 178444389、化合物収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 3.69 g of (trans-4-pentylcyclohexyl)methanol and 5.51 g of triphenylphosphine in 70 ml of methylene chloride at -30° C. was placed under argon gasification and treated portionwise within 15 minutes with 7.30 g of solid tetrabromomethane so that the internal temperature did not exceed -20° C. After completion of the addition, the cooling bath was removed and the mixture was stirred for a further 18 hours with gradual warming to room temperature. The mixture was then concentrated on a rotary evaporator and the semi-crystalline residue obtained was triturated with 200 ml of warm hexane, filtered and the concentrated filtrate was chromatographed with hexane on a column of silica gel. There were obtained 4.79 g (97%) of trans-1-(bromomethyl)-4-pentylcyclohexane as a colourless liquid which was purified further by distillation; b.p. 82° C./0.08 mmHg.

後処理

  1. customat -30° C.
  2. customdid not exceed -20° C
  3. additionAfter completion of the addition
  4. customthe cooling bath was removed
  5. concentrationThe mixture was then concentrated on a rotary evaporator
  6. customthe semi-crystalline residue obtained
  7. customwas triturated with 200 ml of warm hexane
  8. filtrationfiltered
  9. customthe concentrated filtrate was chromatographed with hexane on a column of silica gel

出典と根拠

ORDレコード
ord-29e1e5c72c9c4920aa3331f10548b9b0
出典データセット
uspto-grants-1987_11
特許番号
US04708441

反応ノート

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